PROCEEDINGS OF THE TECHNICAL WORKSHOP ON RADAR SCATTERING FROM RANDOM MEDIA, HELD AT THE UNIVERSITY OF CALIFORNIA, LA JOLLA, CALIFORNIA, 5-16 AUGUST 1968

1968 ◽  
Author(s):  
K. Kresa
Keyword(s):  
Random Media ◽  
University Of California ◽  
Radar Scattering ◽  
La Jolla ◽  
The University

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.

Design

2020 ◽  
pp. 129-141
Author(s):  
Stephen K. Reed
Keyword(s):  
Double Helix ◽  
University Of California ◽  
X Ray Diffraction ◽  
Design Problems ◽  
Goal State ◽  
Helix Structure ◽  
Intermediate States ◽  
Double Helix Structure ◽  
La Jolla ◽  
The University

Many design problems are ill-structured in which the start state, the goal state, and intermediate states are incompletely specified. They do not have right or wrong answers, only better or worse ones. They require decomposition into smaller parts that are revisited as the design progresses. Scientists also confront design problems as they search for nature’s design, such as the structure of DNA. The success of Watson and Crick in discovering its double-helix structure was influenced by their access to X-ray diffraction pictures, ability to interpret these pictures, utilize the relative amounts of bases in the molecule, and recognize that two strands of a molecule provide a mechanism for replication. The Geisel Library on the University of California, San Diego, campus illustrates the combination of function and beauty in designing a building. The Salk Institute in La Jolla, California, is widely acclaimed as a magnificent achievement by Louis Kahn. The addition of the East Building is an example of the challenges encountered in making modifications.

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.

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.

Reactions of Alkenes

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
South China ◽  
Diazonium Salt ◽  
Solvent Free ◽  
University Of California ◽  
University Of Wisconsin ◽  
University Of Technology ◽  
Complementary Approach ◽  
Re Catalyst ◽  
La Jolla ◽  
The University

Ana C. Fernandes of the Instituto Superior Técnico, Lisboa, devised (Tetrahedron Lett. 2010, 51, 1048) an effective Re catalyst for the solvent-free hydrogenation of an alkene 1. Yasushi Imada and Takeshi Naota of Osaka University showed (Organic Lett. 2010, 12, 32) that a flavin could catalyze the hydrogenation of an alkene 3. Note that the thioether was stable under these conditions. Huanfeng Jian of the South China University of Technology developed (J. Org. Chem. 2010, 75, 2321) a Pd-based protocol for the oxidative cleavage of an alkene 5. The cleavage could be halted at the cis diol. K. C. Nicolaou of Scripps/La Jolla optimized (Organic Lett. 2010, 12, 1552) a complemetary cleavage of an alkene 7, again proceeding via the diol. J. R. Falck of UT Southwestern established (J. Org. Chem. 2010, 75, 1701) the Heck-type oxidative silylation of an alkene 9 to the Z -silane 10. Timothy F. Jamison of MIT effected (Chem. Commun. 2010, 46, 907) the borylation of an alkene 11. Kálmán Szabó of Stockholm University reported (Angew. Chem. Int. Ed. 2010, 49, 4051) a complementary approach for effecting the same transformation. Cathleen M. Crudden of Queen’s University, Kingston, observed (J. Am. Chem. Soc. 2010, 132, 131) that Rh-catalyzed hydroboration of 13 delivered the borane 14. Tehshik P. Yoon of the University of Wisconsin used (J. Am. Chem. Soc. 2010, 132, 4570) Fe to catalyze the addition of an oxaziridine 16 to an alkene 15. Yasuhiro Shiraishi of Osaka University improved (J. Org. Chem. 2010, 75, 1450) the photochemical addition of acetone to an alkene 18. Chul-Ho Jun of Yonsei University described (Tetrahedron Lett. 2010, 51, 160) a related procedure. Professor Jamison effected (J. Am. Chem. Soc. 2010, 132, 6880) the branching homologation of an alkene to give 21 . F. Dean Toste of the University of California, Berkeley, accomplished (J. Am. Chem. Soc. 2010, 132, 8885) the oxidative homologation of an alkene to the ester 22. Markus R. Heinrich of the Universität Erlangen-Nürnberg developed (Tetrahedron Lett. 2010, 51, 1758) the tandem addition of the hydroperoxide 23 and a diazonium salt 24, leading to 25.

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