Metal-Mediated C–C Ring Construction: The Ding Synthesis of (−)-Indoxamycin B

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Claisen Rearrangement ◽  
Iron Catalyst ◽  
Gold Catalyst ◽  
State University ◽  
Relative Configuration ◽  
University Of Texas ◽  
Diethyl Zinc ◽  
Single Diastereomer ◽  
The University ◽  
Oregon State University

Shou-Fei Zhu of Nankai University developed (Angew. Chem. Int. Ed. 2014, 53, 13188) an iron catalyst that effected the enantioselective cyclization of 1 to 2. Bypassing diazo precursors, Junliang Zhang of East China Normal University used (Angew. Chem. Int. Ed. 2014, 53, 13751) a gold catalyst to cyclize 3 to 4. Taking advantage of energy transfer from a catalytic Ir complex, Chuo Chen of University of Texas Southwestern carried out (Science 2014, 346, 219) intramolec­ular 2+2 cycloaddition of 5, leading, after dithiane formation, to the cyclobutane 6. Intramolecular ketene cycloaddition has been limited in scope. Liming Zhang of the University of California Santa Barbara found (Angew. Chem. Int. Ed. 2014, 53, 9572) that intramolecular oxidation of an intermediate Ru vinylidene led to a species that cyclized to the cyclobutanone 8. James D. White of Oregon State University devised (J. Am. Chem. Soc. 2014, 136, 13578) an iron catalyst that mediated the enantioselective Conia-ene cyclization of 9 to 10. Xiaoming Feng of Sichuan University observed (Angew. Chem. Int. Ed. 2014, 53, 11579) that the Ni-catalyzed Claisen rearrangement of 11 proceeded with high diastereo- and enantiocontrol. The relative configuration of the product 12 was not reported. Robert H. Grubbs of Caltech showed (J. Am. Chem. Soc. 2014, 136, 13029) that ring opening cross metathesis of 13 with 14 delivered the Z product 15. Mn(III) cyclization has in the past required a stoichiometric amount of inorganic oxidant. Sangho Koo of Myong Ji University found (Adv. Synth. Catal. 2014, 356, 3059) that by adding a Co co- catalyst, air could serve as the stoichiometric oxidant. Indeed, 16 could be cyclized to 17 using inexpensive Mn(II). Matthias Beller of the Leibniz-Institüt für Katalyse prepared (Angew. Chem. Int. Ed. 2014, 53, 13049) the cyclohexene 20 by coupling the racemic alcohol 18 with the amine 19. Paultheo von Zezschwitz of Philipps-Universität Marburg added (Chem. Commun. 2014, 50, 15897) diethyl zinc in a conjugate sense to 21, then reduced the product to give 22. Depending on the reduction method, either diastereomer of the product could be made dominant. Nuno Maulide of the University of Vienna dis­placed (Angew. Chem. Int. Ed. 2014, 53, 7068) the racemic chloride 23 with diethyl zinc to give 24 as a single diastereomer.

C-O Ring Containing Natural Products: Paeonilactone B (Taylor), Deoxymonate B (de la Pradilla), Sanguiin H-5 (Spring), Solandelactone A (White), Spirastrellolide A (Paterson)

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Oxidative Coupling ◽  
Claisen Rearrangement ◽  
Cyclic Carbonate ◽  
Membered Ring ◽  
State University ◽  
Enantiomerically Pure ◽  
University Of Cambridge ◽  
Spirastrellolide A ◽  
The University ◽  
Oregon State University

Richard J. K. Taylor of the University of York has developed (Angew. Chem. Int. Ed. 2008, 47, 1935) the diasteroselective intramolecular Michael cyclization of phosphonates such as 2. Quenching of the cyclized product with paraformaldehyde delivered ( + )-Paeonilactone B 3. Roberto Fernández de la Pradilla of the CSIC, Madrid established (Tetrahedron Lett. 2008, 49, 4167) the diastereoselective intramolecular hetero Michael addition of alcohols to enantiomerically-pure acyclic sulfoxides such as 4 to give the allylic sulfoxide 5. Mislow-Evans rearrangement converted 5 into 6, the enantiomerically-pure core of Ethyl Deoxymonate B 7. The ellagitannins, represented by 10, are single atropisomers around the biphenyl linkage. David R. Spring of the University of Cambridge found (Organic Lett. 2008, 10, 2593) that the chiral constraint of the carbohydrate backbone of 9 directed the absolute sense of the oxidative coupling of the mixed cuprate derived from 9, leading to Sanguiin H-5 10 with high diastereomeric control. A key challenge in the synthesis of the solandelactones, exemplified by 14, is the stereocontrolled construction of the unsaturated eight-membered ring lactone. James D. White of Oregon State University found (J. Org. Chem. 2008, 73, 4139) an elegant solution to this problem, by exposure of the cyclic carbonate 11 to the Petasis reagent, to give 12. Subsequent Claisen rearrangement delivered the eight-membered ring lactone, at the same time installing the ring alkene of Solandelactone E 14. AD-mix usually proceeds with only modest enantiocontrol with terminal alkenes. None the less, Ian Paterson, also of the University of Cambridge, observed (Angew. Chem. Int. Ed. 2008, 47, 3016, Angew. Chem. Int. Ed. 2008, 47, 3021) that bis-dihydroxylation of the diene 17 proceeded to give, after acid-mediated cyclization, the bis-spiro ketal core 18 of Spirastrellolide A Methyl Ester 19 with high diastereocontrol.

Functional Group Protection: The Pohl Synthesis of β-1,4-Mannuronate Oligomers

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Iron Catalyst ◽  
Gold Catalyst ◽  
State University ◽  
Allyl Ester ◽  
National Chemical Laboratory ◽  
Chemical Laboratory ◽  
Benzyl Ethers ◽  
Institute Of Technology ◽  
Tokyo Medical ◽  
The University

D. Srinivasa Reddy of the National Chemical Laboratory converted (Org. Lett. 2015, 17, 2090) the selenide 1 to the alkene 2 under ozonolysis conditions. Takamitsu Hosoya of the Tokyo Medical and Dental University found (Chem. Commun. 2015, 51, 8745) that even highly strained alkynes such as 4 can be generated from a sulfinyl vinyl triflate 3. An alkyne can be protected as the dicobalt hexacarbonyl complex. Joe B. Gilroy and Mark S. Workentin of the University of Western Ontario found (Chem. Commun. 2015, 51, 6647) that following click chemistry on a non-protected distal alkyne, deprotection of 5 to 6 could be effected by exposure to TMNO. Stefan Bräse of the Karlsruhe Institute of Technology and Irina A. Balova of Saint Petersburg State University showed (J. Org. Chem. 2015, 80, 5546) that the bend of the Co complex of 7 enabled ring-closing metathesis, leading after deprotection to 8. Morten Meldal of the University of Copenhagen devised (Eur. J. Org. Chem. 2015, 1433) 9, the base-labile protected form of the aldehyde 10. Nicholas Gathergood of Dublin City University and Stephen J. Connon of the University of Dublin developed (Eur. J. Org. Chem. 2015, 188) an imidazolium catalyst for the exchange deprotection of 11 to 13, with the inexpensive aldehyde 12 as the acceptor. Peter J. Lindsay-Scott of Eli Lilly demonstrated (Org. Lett. 2015, 17, 476) that on exposure to KF, the isoxa­zole 14 unraveled to the nitrile 15. Masato Kitamura of Nagoya University observed (Tetrahedron 2015, 71, 6559) that the allyl ester of 16 could be removed to give 17, with the other alkene not affected. Benzyl ethers are among the most common of alcohol protecting groups. Yongxiang Liu and Maosheng Cheng of Shenyang Pharmaceutical University showed (Adv. Synth. Catal. 2015, 357, 1029) that 18 could be converted to 19 simply by expo­sure to benzyl alcohol in the presence of a gold catalyst. Reko Leino of Åbo Akademi University developed (Synthesis 2015, 47, 1749) an iron catalyst for the reductive benzylation of 20 to 21. Related results (not illustrated) were reported (Org. Lett. 2015, 17, 1778) by Chae S. Yi of Marquette University.

Arrays of Stereogenic Centers: The Yadav Synthesis of Nhatrangin A

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Claisen Rearrangement ◽  
Iron Catalyst ◽  
Aldol Condensation ◽  
State University ◽  
Max Planck ◽  
Chiral Amine ◽  
Cornell University ◽  
University Of Oxford ◽  
Enantioselective Epoxidation ◽  
The University

Miquel Costas of the Universitat de Girona developed (J. Am. Chem. Soc. 2013, 135, 14871) an iron catalyst for the enantioselective epoxidation of the Z-ester 1 to 2. Although the α-chloro aldehyde derived from 3 epimerized under the reaction conditions, Robert Britton of Simon Fraser University showed (Org. Lett. 2013, 15, 3554) that the subsequent aldol condensation with 4 favored one enantiomer, leading to 5 in high ee. Other selective aldol condensations of 4 (not illustrated) have been reported by Zorona Ferjancic and Radomir N. Saicic of the University of Belgrade (Eur. J. Org. Chem. 2013, 5555) and by Tomoya Machinami of Meisei University (Synlett 2013, 24, 1501). Motomu Kanai of the University of Tokyo condensed (Org. Lett. 2013, 15, 4130) D-arabinose 6 with diallyl amine and the alkyne 7 to give the amine 8 as a mixture of diastereomers. Naoya Kumagai and Masakatsu Shibasaki of the Institute of Microbial Chemistry combined (Angew. Chem. Int. Ed. 2013, 52, 7310) 9 and 10 to prepare the α-chiral amine 11. Tomoya Miura and Masahiro Murakami of Kyoto University used (J. Am. Chem. Soc. 2013, 135, 11497) an Ir catalyst to migrate the alkene of 13 to the E allyl boro­nate, that then added to 12 to give 14. Gong Chen of Pennsylvania State University alkylated (J. Am. Chem. Soc. 2013, 135, 12135) the β-H of 15 with 16 to give selec­tively the diastereomer 17. Geoffrey W. Coates of Cornell University devised (J. Am. Chem. Soc. 2013, 135, 10930) catalysts for the carbonylation of the epoxide 18 to either regioisomer of the β-lactone 19. Yujiro Hayashi of Tohoku University combined (Chem. Lett. 2013, 42, 1294) the inexpensive succinaldehyde 20 and ethyl glyoxylate 21 to give the versatile aldehyde 22. Nuno Maulide of the Max-Planck-Institut für Kohlenforschung Mülheim effected (J. Am. Chem. Soc. 2013, 135, 14968) Claisen rearrangement of 23 to give, after reduc­tion and hydrolysis, the aldehyde 24. Stephen G. Davies of the University of Oxford reported (Chem. Commun. 2013, 49, 7037) a related Claisen rearrangement (not illustrated). Ying-Chun Chen of Sichuan University devised (Org. Lett. 2013, 15, 4786) the cascade combination of 25 and 26 to give 27.

Arrays of Stereogenic Centers: The Davies Synthesis of Acosamine

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Conjugate Addition ◽  
Michigan State University ◽  
State University ◽  
One Pot ◽  
Relative Configuration ◽  
University Of Texas ◽  
Stereogenic Centers ◽  
National University ◽  
The University ◽  
Mediated Oxidation

Babak Borhan of Michigan State University found (Angew. Chem. Int. Ed. 2011, 50, 2593) that the ligand developed for asymmetric osmylation worked well for the enantioselective cyclization of 1 to 2. Kyungsoo Oh of IUPUI devised (Org. Lett. 2011, 13, 1306) a Co catalyst for the stereocontrolled addition of 4 to 3 to give 5. Michael J. Krische of the University of Texas Austin prepared (Angew. Chem. Int. Ed. 2011, 50, 3493) 8 by Ir*-mediated oxidation/addition of 7 to 6. Yixin Lu of the National University of Singapore employed (Angew. Chem. Int. Ed. 2011, 50, 1861) an organocatalyst to effect the stereocontrolled addition of 10 to 9. Naoya Kumagai and Masakatsu Shibasaki of the Institute of Microbial Chemistry, Tokyo took advantage (J. Am. Chem. Soc. 2011, 133, 5554) of the soft Lewis basicity of 13 to effect stereocontrolled condensation with 12. Yujiro Hayashi of the Tokyo University of Science found (Angew. Chem. Int. Ed. 2011, 50, 2804, not illustrated) that aqueous chloroacetaldehyde participated well in crossed aldol condensations. Andrew V. Malkov, now at Loughborough University, and Pavel Kocovsky of the University of Glasgow showed (J. Org. Chem. 2011, 76, 4800) that the inexpensive mixed crotyl silane 16 could be added to 15 with high stereocontrol. Shigeki Matsunaga of the University of Tokyo and Professor Shibasaki opened (J. Am. Chem. Soc. 2011, 133, 5791) the meso aziridine 18 with malonate 19 to give 20. Masahiro Terada of Tohoku University effected (Org. Lett. 2011, 13, 2026) the conjugate addition of 22 to 21 with high stereocontrol. Jinxing Ye of the East China University of Science and Technology reported (Angew. Chem. Int. Ed. 2011, 50, 3232, not illustrated) a related conjugate addition. Kian L. Tian of Boston College observed (Org. Lett. 2011, 13, 2686) that the kinetic hydroformylation of 24 set the relative configuration of two stereogenic centers. Alexandre Alexakis and Clément Mazet of the Université de Genève established (Angew. Chem. Int. Ed. 2011, 50, 2354) a tandem one-pot procedure for the addition of 26 to 27 to give 28.

scholarly journals Why Age Matters to Higher Education: Age-Friendly Tools and Techniques for Culture Change

2020 ◽  
Vol 4 (Supplement_1) ◽  
pp. 551-551
Author(s):  
David Burdick ◽  
Karen Rose ◽  
Dana Bradley
Keyword(s):  
University Presidents ◽  
Steering Committee ◽  
State University ◽  
Community Members ◽  
University Leadership ◽  
Drexel University ◽  
College Of Nursing ◽  
Tools And Techniques ◽  
The University ◽  
Oregon State University

Abstract Momentum is growing for the Age-Friendly University Network as proponents, primarily gerontology educators, have successfully encouraged university presidents to sign nonbinding pledged to become more age-friendly in programs and policies, endorsing 10 Age-Friendly University Principles. While this trend is inspiring, more is needed to fully achieve benefits for universities, students, communities, and older adults. Four presentations discuss innovative ways of deepening university commitment, weaving the principles into the fabric of the university. The first paper describes thematic content analysis from five focus groups with admissions and career services staff at Washington University in St. Louis and the recommendations that emerged for the provision of programs and services for post-traditional students. The second paper describes efforts to utilize community-impact internships and community partnerships to build support for Age-Friendly University initiatives at Central Connecticut State University, particularly in the context of the university’s recent Carnegie Foundation Engaged Campus designation. The third paper describes how Drexel University became Philadelphia’s first Age-Friendly University and current efforts in the Drexel College of Nursing and Heatlh Care Profession’s AgeWell Collaboratory to convene university-wide leadership for an AFU Steering Committee working on four mission-driven efforts to ensure AFU sustainability. The fourth paper describes steps taken by AFU proponents at Western Oregon State University to gain endorsement from university leadership and community, including mapping the 10 AFU Principles to the university’s strategic plan, faculty senate endorsement, and survey/interview results of older community members’ use of the university, which collectively have enhanced deeper and broader campus buy-in of AFU.

Functional Group Transformations

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Gold Catalyst ◽  
Sulfonyl Chloride ◽  
Allylic Alcohol ◽  
West Virginia University ◽  
Israel Institute ◽  
University Of Texas ◽  
Amino Amide ◽  
Cu Catalyst ◽  
Institute Of Technology ◽  
The University

Mark Gandelman of the Technion–Israel Institute of Technology devised (Adv. Synth. Catal. 2011, 353, 1438) a protocol for the decarboxylative conversion of an acid 1 to the iodide 3. Doug E. Frantz of the University of Texas, San Antonio effected (Angew. Chem. Int. Ed. 2011, 50, 6128) conversion of a β-keto ester 4 to the diene 5 by way of the vinyl triflate. Pei Nian Liu of the East China University of Science and Technology and Chak Po Lau of the Hong Kong Polytechnic University (Adv. Synth. Catal. 2011, 353, 275) and Robert G. Bergman and Kenneth N. Raymond of the University of California, Berkeley (J. Am. Chem. Soc. 2011, 133, 11964) described new Ru catalysts for the isomerization of an allylic alcohol 6 to the ketone 7. Xiaodong Shi of West Virginia University optimized (Adv. Synth. Catal. 2011, 353, 2584) a gold catalyst for the rearrangement of a propargylic ester 8 to the enone 9. Xue-Yuan Liu of Lanzhou University used (Adv. Synth. Catal. 2011, 353, 3157) a Cu catalyst to add the chloramine 11 to the alkyne 10 to give 12. Kasi Pitchumani of Madurai Kamaraj University converted (Org. Lett. 2011, 13, 5728) the alkyne 13 into the α-amino amide 15 by reaction with the nitrone 14. Katsuhiko Tomooka of Kyushu University effected (J. Am. Chem. Soc. 2011, 133, 20712) hydrosilylation of the propargylic ether 16 to the alcohol 17. Matthew J. Cook of Queen’s University Belfast (Chem. Commun. 2011, 47, 11104) and Anna M. Costa and Jaume Vilarrasa of the Universitat de Barcelona (Org. Lett. 2011, 13, 4934) improved the conversion of an alkenyl silane 18 to the iodide 19. Vinay Girijavallabhan of Merck/Kenilworth developed (J. Org. Chem. 2011, 76, 6442) a Co catalyst for the Markovnikov addition of sulfide to an alkene 20. Hojat Veisi of Payame Noor University oxidized (Synlett 2011, 2315) the thiol 22 directly to the sulfonyl chloride 23. Nicholas M. Leonard of Abbott Laboratories prepared (J. Org. Chem. 2011, 76, 9169) the chromatography-stable O-Su ester 25 from the corresponding acid 24.

Organocatalyzed C–C Ring Construction: The Mihovilovic Synthesis of Piperenol B

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
State University ◽  
Air Oxidation ◽  
Microbial Oxidation ◽  
Max Planck ◽  
National Chemical Laboratory ◽  
Chemical Laboratory ◽  
Northwestern University ◽  
National University ◽  
The University ◽  
Oregon State University

M. Kevin Brown of Indiana University prepared (J. Am. Chem. Soc. 2015, 137, 3482) the cyclobutane 3 by the organocatalyzed addition of 2 to the alkene 1. Karl Anker Jørgensen of Aarhus University assembled (J. Am. Chem. Soc. 2015, 137, 1685) the complex cyclobutane 7 by the addition of 5 to the acceptor 4, followed by conden­sation with the phosphorane 6. Zhi Li of the National University of Singapore balanced (ACS Catal. 2015, 5, 51) three enzymes to effect enantioselective opening of the epoxide 8 followed by air oxidation to 9. Gang Zhao of the Shanghai Institute of Organic Chemistry and Zhong Li of the East China University of Science and Technology added (Org. Lett. 2015, 17, 688) 10 to 11 to give 12 in high ee. Akkattu T. Biju of the National Chemical Laboratory combined (Chem. Commun. 2015, 51, 9559) 13 with 14 to give the β-lactone 15. Paul Ha-Yeon Cheong of Oregon State University and Karl A. Scheidt of Northwestern University reported (Chem. Commun. 2015, 51, 2690) related results. Dieter Enders of RWTH Aachen University constructed (Chem. Eur. J. 2015, 21, 1004) the complex cyclopentane 20 by the controlled com­bination of 16, 17, and 18, followed by addition of the phosphorane 19. Derek R. Boyd and Paul J. Stevenson of Queen’s University Belfast showed (J. Org. Chem. 2015, 80, 3429) that the product from the microbial oxidation of 21 could be protected as the acetonide 22. Ignacio Carrera of the Universidad de la República described (Org. Lett. 2015, 17, 684) the related oxidation of benzyl azide (not illustrated). Manfred T. Reetz of the Max-Planck-Institut für Kohlenforschung and the Philipps-Universität Marburg found (Angew. Chem. Int. Ed. 2014, 53, 8659) that cytochrome P450 could oxidize the cyclohexane 23 to the cyclohexanol 24. F. Dean Toste of the University of California, Berkeley aminated (J. Am. Chem. Soc. 2015, 137, 3205) the ketone 25 with 26 to give 27. Benjamin List, also of the Max-Planck-Institut für Kohlenforschung, reported (Synlett 2015, 26, 1413) a parallel investigation. Philip Kraft of Givaudan Schweiz AG and Professor List added (Angew. Chem. Int. Ed. 2015, 54, 1960) 28 to 29 to give 30 in high ee.

Alkaloid Synthesis: (−)-L-Batzellaside A (Toyooka), Limazepine A (Zemribo), (+)-Febrifugine (Pansare), Amathaspiramide F (Tambar), Allomatrine (Brown), Lyconadine C (Waters), Tabersonine (Andrade)

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Absolute Configuration ◽  
Claisen Rearrangement ◽  
Medical Center ◽  
University Of Texas ◽  
Temple University ◽  
Lycopodium Alkaloid ◽  
Alkaloid Synthesis ◽  
The University ◽  
Acyl Azide ◽  
Stereogenic Center

Naoki Toyooka of the University of Toyama prepared (Eur. J. Org. Chem. 2013, 2841) the lactam 1 from commercial tri-O-benzyl-D-glucal. Reduction with Dibal followed by coupling of the intermediate with allyltrimethylsilane delivered the piper­idine 2, that was carried on to (−)-L-batzellaside A 3. Ronalds Zemribo of the Latvian Institute of Organic Synthesis effected (Org. Lett. 2013, 15, 4406) Ireland–Claisen rearrangement of the lactone 4 to give the pyrroli­dine 5 with high geometric control. This was readily converted to limazepine E 6. Sunil V. Pansare of Memorial University used (Synthesis 2013, 45, 1863) an organo­catalyst to set the relative and absolute configuration in the addition of 7 to 8 to give 9. The acyclic stereogenic center of 9 was inverted twice en route to (+)-febrifugine 10. Uttam K. Tambar of the University of Texas Southwestern Medical Center combined (Org. Lett. 2013, 15, 5138) 11 with 12 under Pd catalysis to set the rel­ative configuration of 13. Late-stage bromination completed the synthesis of amathaspiramide F 14. Richard C. D. Brown of the University of Southampton used (Org. Lett. 2013, 15, 4596) the sulfinylimine of 15 to direct the stereochemical sense of the addition of 16. The product 17 was carried over several steps to the tetracyclic alkaloid allomatrine 18. Stephen P. Waters of the University of Vermont devised (Org. Lett. 2013, 15, 4226) what appears to be a general route to pyridones. On warming, the acyl azide derived from the acid 19 rearranged to the isocyanate, that cyclized to the pyridone 20. Deprotection led to the Lycopodium alkaloid lyconadin C 21. Among the several creative routes to indole alkaloids that have been put forward in recent months, the synthesis of tabersonine 25 (J. Am. Chem. Soc. 2013, 135, 13334) by Rodrigo B. Andrade of Temple University stands out. Deprotonation of 22 led to an anion that was condensed with 23 to give 24, with the relative and absolute configuration directed by the pendant sulfinylimine. In addition to tabersonine, the intermediate 24 was carried on to vincadifformine and to aspidospermidine.

Congratulations! The Second JDR Award

2017 ◽  
Vol 12 (2) ◽  
pp. 222-222
Author(s):  
Editors-in-Chief ◽  
Haruo Hayashi
Keyword(s):  
State University ◽  
Award Winner ◽  
Award Ceremony ◽  
Future Success ◽  
The University ◽  
Oregon State University

The second JDR Award ceremony was held in Kasumigaseki, Japan, at November 22, 2016 and the certificate was given to the JDR award winner, Prof. Harry Yeh of Oregon State University (Prof. Shinji Sato of the University of Tokyo received it as a dupty). We congratulate the winner and sincerely wish for future success.

C–H Functionalization: The Snyder Synthesis of (+)-Scholarisine A

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Unsaturated Ester ◽  
State University ◽  
University Of Minnesota ◽  
University Of Texas ◽  
Princeton University ◽  
Fe Catalyst ◽  
Peking University ◽  
Lanzhou Institute ◽  
Related Approach ◽  
The University

Thomas R. Hoye of the University of Minnesota devised (Nature 2013, 501, 531) the reagent 2, that cyclized to a benzyne that in turn dehydrogenated the alkane 1 to the alkene 3, and 4. Abigail G. Doyle of Princeton University developed (J. Am. Chem. Soc. 2013, 135, 12990) a reagent combination for the allylic fluorination of a terminal alkene 5 to the branched product 6. Yan Zhang and Jianbo Wang of Peking University oxidized (Angew. Chem. Int. Ed. 2013, 52, 10573) the methyl group of 7 to give the nitrile 8. Hanmin Huang of the Lanzhou Institute of Chemical Physics found (Org. Lett. 2013, 15, 3370) conditions for the carbonylation of the benzylic site of 9, leading to coupling with 10 to form the amide 11. Yu Rao of Tsinghua University effected (Angew. Chem. Int. Ed. 2013, 52, 13606) the direct methoxylation of 12, to give 13. Pd-mediated methoxylation had previously been described (Chem. Sci. 2013, 4, 4187) by Bing-Feng Shi of Zhejiang University. M. Christina White of the University of Illinois, Urbana found (J. Am. Chem. Soc. 2013, 135, 14052) that with variant ligands on the Fe catalyst, the oxidation of 14 could be directed selectively to either 15 or 16. C–H bonds can also be converted to C–N bonds. Sukbok Chang of KAIST oxi­dized (J. Am. Chem. Soc. 2013, 135, 12861) the unsaturated ester 17 with 18 to form the enamide 18. Gong Chen of Pennsylvania State University cyclized (Angew. Chem. Int. Ed. 2013, 52, 11124) the amide 20 to the γ-lactam 21. Professor Shi reported (Angew. Chem. Int. Ed. 2013, 52, 13588) a related approach to β-lactams. Ethers are easily oxidized. Taking advantage of this, Yun Liang of Hunan Normal University coupled (Synthesis 2013, 45, 3137) the bromoalkyne 23 with tetrahydro­furan 22 to give 24. Guangbin Dong of the University of Texas, Austin devised (J. Am. Chem. Soc. 2013, 135, 17747) a protocol for the β-arylation of ketones, includ­ing the preparation of 27 by the coupling of 25 with 26.

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