C–H Functionalization: The Hatakeyama Synthesis of (–)-Kaitocephalin

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
University Of California ◽  
University Of Delaware ◽  
State University ◽  
Max Planck ◽  
Pennsylvania State University ◽  
University Of Illinois ◽  
University Of Houston ◽  
Hydride Abstraction ◽  
La Jolla ◽  
The University

John F. Hartwig of the University of California, Berkeley showed (Nature 2012, 483, 70) that intramolecular C–H silylation of 1 selectively gave, after oxidation and acetylation, the bis acetate 2. Gong Chen of Pennsylvania State University coupled (J. Am. Chem. Soc. 2012, 134, 7313) 3 with 4 to give the ether 5. M. Christina White of the University of Illinois effected (J. Am. Chem. Soc. 2012, 134, 9721) selective oxidation of the taxane derivative 6 to the lactone 7. Most of the work on C–H functionalization has focused on the formation of C–C, C–O, and C–N bonds. Donald A. Watson of the University of Delaware developed (Angew. Chem. Int. Ed. 2012, 51, 3663) conditions for the complementary conversion of an alkene 8 to the allyl silane 9, a powerful and versatile nucleophile. Kilian Muniz of ICIQ Tarragona oxidized (J. Am. Chem. Soc. 2012, 134, 7242) the enyne 10 selectively to the amine 11. Phil S. Baran of Scripps/La Jolla devised (J. Am. Chem. Soc. 2012, 134, 2547) a protocol for the OH-directed amination of 12 to 13. Professor White developed (J. Am. Chem. Soc. 2012, 134, 2036) a related OH-directed amination of 14 to 15 that proceeded with retention of absolute configuration. Tom G. Driver of the University of Illinois, Chicago showed (J. Am. Chem. Soc. 2012, 134, 7262) that the aryl azide 16 could be cyclized directly to the amine, which was protected to give 17. As illustrated by the conversion of 18 to 20 devised (Adv. Synth. Catal. 2012, 354, 701) by Martin Klussmann of the Max-Planck-Institut, Mülheim, C–H functionalization can be accomplished by hydride abstraction followed by coupling of the resulting carbocation with a nucleophile. Olafs Daugulis of the University of Houston used (Angew. Chem. Int. Ed. 2012, 51, 5188) a Pd catalyst to couple 21 with 22 to give 23 with high diastereocontrol. Yoshiji Takemoto of Kyoto University cyclized (Angew. Chem. Int. Ed. 2012, 51, 2763) the chloroformate 24 directly to the oxindole 25.

Synthesis of Substituted Benzenes: The Carter Synthesis of Siamenol

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Aryl Halides ◽  
Substituted Benzenes ◽  
Diversity Oriented Synthesis ◽  
University Of Illinois ◽  
University Of Houston ◽  
Direct Functionalization ◽  
University Of Edinburgh ◽  
Aryl Tosylates ◽  
La Jolla ◽  
The University

Tosylates are among the least expensive, but also among the least reactive toward Pd(0) oxidative addition, of aryl sulfonates. Jie Wu of Fudan University has now devised conditions (J. Org. Chem. 2007, 72, 9346) for the Pd-catalyzed coupling of aryl tosylates such as 1 with arene trifluoroborates. Kei Manabe of RIKEN has found (Organic Lett. 2007, 9, 5593) that an ortho OH activates an adjacent Cl for Pd-mediated coupling, allowing the conversion of 4 to 6 . Philippe Uriac and Pierre van de Weghe of the Université de Rennes I have developed (Organic Lett. 2007, 9, 3623) conditions for the catalytic acylation of aryl halides with alkenyl acetates such as 8. Multi-component coupling lends itself well to diversity-oriented synthesis. As illustrated by the combination of 10 with 11 and 12 to give 13 reported (Organic Lett. 2007, 9, 5589) by Michael F. Greaney of the University of Edinburgh, benzynes can do double addition with high regiocontrol. For other recent references to unsymmetrical double additions to arynes, see Angew.Chem. Int. Ed. 2007, 46, 5921; Chem. Commun. 2007, 2405; and J. Am. Chem. Soc. 2006, 128, 14042. C-H functionalization of arenes is of increasing importance. John F. Hartwig of the University of Illinois has described (Organic Lett. 2007, 9, 757; 761) improved conditions for Ir-catalyzed meta borylation, and conditions for further coupling of the initial borate 16 to give amines such as 17. Lei Liu and Qing-Xiang Guo of the University of Science and Technology, Hefei have found (Tetrahedron Lett. 2007, 48, 5449) that oxygen can be used as the stoichiometric oxidant in the Pd-catalyzed functionalization of H’s ortho to anilides. Two other research groups (J. Am. Chem. Soc. 2007, 129, 6066; Angew. Chem. Int. Ed. 2007, 46, 5554; J. Org. Chem. 2007, 72, 7720) reported advances in this area. In a close competition, Jin-Quan Yu, now at Scripps/La Jolla (J. Am. Chem. Soc. 2007, 129, 3510) and Olafs Daugulis of the University of Houston (J. Am. Chem. Soc. 2007, 129, 9879) both reported that a carboxyl group can activate an ortho H for direct functionalization.

Heteroaromatic Construction: The Fukuyama Synthesis of Tryprostatin A

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Organic Chemistry ◽  
University Of California ◽  
University Of Arkansas ◽  
Yale University ◽  
Au Catalyst ◽  
University Of Houston ◽  
Selective Substitution ◽  
Mcgill University ◽  
La Jolla ◽  
The University

Alessandro Palmieri of the University of Camerino developed (Synlett 2010, 2468) the condensation of a nitro acrylate 1 with a 1,3-dicarbonyl partner 2 to give the furan 3. Chaozhong Li of the Shanghai Institute of Organic Chemistry showed (Tetrahedron Lett. 2010, 51, 3678) that an alkenyl halide 4 could be cyclized to the furan 5. Ayhan S. Demir of Middle East Technical University established (Chem. Commun. 2010, 46, 8032) that a Au catalyst could catalyze the addition of an amine 7 to a cyanoester 6 to give the pyrrole 8 . Bruce A. Arndtsen of McGill University effected (Org. Lett. 2010, 12, 4916) the net three-component coupling of an imine 9, an acid chloride 10, and an alkyne 11 to deliver the pyrrole 12. Bernard Delpech of CNRS Gif-sur-Yvette prepared (Org. Lett. 2010, 12, 4760) the pyridine 15 by combining the diene 13 with the incipient carbocation 14. Max Malacria, Vincent Gandon, and Corinne Aubert of UPMC Paris optimized (Synlett 2010, 2314) the internal Co-mediated cyclization of a nitrile alkyne 5 to the tetrasubstituted pyridine 17. Yoshiaki Nakao of Kyoto University and Tamejiro Hiyama, now at Chuo University, effected (J. Am. Chem. Soc. 2010, 132, 13666) selective substitution of a preformed pyridine 18 at the C-4 position by coupling with an alkene 19. We showed (J. Org. Chem. 2010, 75, 5737) that the anion from deprotonation of a pyridine 21 could be added in a conjugate sense to 22 to give 23. Other particularly useful strategies for further substitution of preformed pyridines have been described by Olafs Daugulis of the University of Houston (Org. Lett. 2010, 12, 4277), by Phil S. Baran of Scripps/La Jolla (J. Am. Chem. Soc. 2010, 132, 13194), and by Robert G. Bergmann of the University of California, Berkeley, and Jonathan A. Ellman of Yale University (J. Org. Chem. 2010, 75, 7863). K. C. Majumdar of the University of Kalyani developed (Tetrahedron Lett. 2010, 51, 3807) the oxidative Pd-catalyzed cylization of 24 to the indole 25. Nan Zheng of the University of Arkansas showed (Org. Lett. 2010, 12, 3736) that Fe could be used to catalyze the rearrangement of the azirine 26 to the indole 27.

C–H Functionalization: The Maimone Synthesis of Podophyllotoxin

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
University Of California ◽  
University Of Illinois ◽  
Methyl Group ◽  
Du Bois ◽  
Princeton University ◽  
University Of Cambridge ◽  
Rh Catalyst ◽  
Institute Of Technology ◽  
La Jolla ◽  
The University

Matthias Beller of the Universität Rostock developed (Angew. Chem. Int. Ed. 2014, 53, 6477) a Rh catalyst for the acceptorless dehydrogenation of an alkane 1 to the alkene 2. Bhisma K. Patel of the Indian Institute of Technology Guwahati effected (Org. Lett. 2014, 16, 3086) oxidation of cyclohexane 3 and 4 to form the allylic benzoate 5. Justin Du Bois of Stanford University devised (Chem. Sci. 2014, 5, 656) an organocatalyst that mediated the hydroxylation of 6 to 7. Vladimir Gevorgyan of the University of Illinois, Chicago hydrosilylated (Nature Chem. 2014, 6, 122) 8 to give an intermediate that, after Ir-catalyzed intramolecular C–H functionalization followed by oxidation, was converted to the diacetate 9. Sukbok Chang of KAIST used (J. Am. Chem. Soc. 2014, 136, 4141) the methoxime of 10 to direct selective amination of the adjacent methyl group, leading to 11. John F. Hartwig of the University of California, Berkeley effected (J. Am. Chem. Soc. 2014, 136, 2555) diastereoselective Cu-catalyzed amination of 12 with 13 to make 14. David W. C. MacMillan of Princeton University accomplished (J. Am. Chem. Soc. 2014, 136, 6858) β-alkylation of the aldehyde 15 with acrylonitrile 16 to give 17. Yunyang Wei of the Nanjing University of Science and Technology alkenylated (Chem. Sci. 2014, 5, 2379) cyclohexane 3 with the styrene 18, leading to 19. Bin Wu of the Kunming Institute of Botany described (Org. Lett. 2014, 16, 480) the Pd-mediated cyclization of 20 to 21. Similar results using Cu catalysis were reported (Angew. Chem. Int. Ed. 2014, 53, 3496, 3706) by Yoichiro Kuninobu and Motomu Kanai of the University of Tokyo and by Haibo Ge of IUPUI. Jin-Quan Yu of Scripps La Jolla constructed (J. Am. Chem. Soc. 2014, 136, 5267) the lactam 24 by γ-alkenyl­ation of the amide 22 with 23, followed by cyclization. Philippe Dauban of CNRS Gif-sur-Yvette prepared (Eur. J. Org. Chem. 2014, 66) the useful crystalline chiron 27 by asymmetric amination of the enol triflate 26 with 25. Matthew J. Gaunt of the University of Cambridge showed (J. Am. Chem. Soc. 2014, 136, 8851) that the phenylative cyclization of 28 with 29 to 30 proceeded with near-perfect retention of absolute configuration.

Five Decades of Research Experience in Speech Anatomy and Physiology

2016 ◽  
Vol 1 (5) ◽  
pp. 4-12
Author(s):  
David P. Kuehn
Keyword(s):  
Ohio State University ◽  
State University ◽  
Research Experience ◽  
University Of Iowa ◽  
University Of Illinois ◽  
Anatomy And Physiology ◽  
The Ohio State University ◽  
Speech Science ◽  
The University ◽  
East Carolina University

This report highlights some of the major developments in the area of speech anatomy and physiology drawing from the author's own research experience during his years at the University of Iowa and the University of Illinois. He has benefited greatly from mentors including Professors James Curtis, Kenneth Moll, and Hughlett Morris at the University of Iowa and Professor Paul Lauterbur at the University of Illinois. Many colleagues have contributed to the author's work, especially Professors Jerald Moon at the University of Iowa, Bradley Sutton at the University of Illinois, Jamie Perry at East Carolina University, and Youkyung Bae at the Ohio State University. The strength of these researchers and their students bodes well for future advances in knowledge in this important area of speech science.

William Alfred Shack

2018 ◽  
pp. 27-36
Author(s):  
Dallas L. Browne
Keyword(s):  
Graduate Students ◽  
Field Research ◽  
University Of California ◽  
University Of Illinois ◽  
Distinguished Career ◽  
The University

This chapter focuses on the life and accomplishments of Africanist anthropologist William Shack. Known to all as Shack, he had a career that included field research in Ethiopia and Swaziland, teaching in African universities as well as at the University of Illinois and the University of California, Berkeley. This chapter can offer hope and encouragement to graduate students of anthropology who may be in departments that are not as supportive or encouraging as they might wish, because William Shack faced major obstacles in completing his Ph.D. Despite the obstacles he faced, Shack went on to a distinguished career as an anthropologist and university administrator.

The Children’s Digital Media Center @ Los Angeles

2012 ◽  
pp. 64-76
Author(s):  
Kaveri Subrahmanyam ◽  
Adriana Manago
Keyword(s):  
Los Angeles ◽  
Digital Media ◽  
Social Networking Sites ◽  
California State University ◽  
University Of California ◽  
State University ◽  
Chat Rooms ◽  
Media Center ◽  
The University

The Children’s Digital Media Center @ Los Angeles studies young people’s interactions with digital media – with a focus on the implications of these interactions for their offline lives and long-term development. Founded by Professor Patricia Greenfield, Distinguished Professor at the University of California, Los Angeles (UCLA), USA, the Center is a collaborative effort of researchers at the UCLA and the California State University, Los Angeles, USA. CDMC@LA researchers have been at the forefront of research on children’s and adolescents’ use of media ranging from early media forms such as television and video games to more recent ones including various applications on the Internet such as chat rooms, social networking sites, and YouTube. This entry presents an overview of the Center – its history, researchers and collaborators, research focus, and major contributions.

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