Welwistatin support studies: Expansion and limitation of aryllead(IV) coupling reactions

被引：38

作者：

Xia, Jibo ^{[1
]}

Brown, Lauren E. ^{[1
]}

Konopelski, Joseph P. ^{[1
]}

机构：

[1] Univ Calif Santa Cruz, Dept Chem & Biochem, Santa Cruz, CA 95064 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 18期

关键词：

D O I：

10.1021/jo071156l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Recent support studies on the total synthesis of the welwistatin system are described. The target step involves lead-mediated arylation of sterically demanding aryl groups and carbon acid coupling partners in order to establish the highly congested tetracyclic core structure. Type 7 beta-ketoesters and beta-ketonitriles were successfully arylated with a variety of ortho- and meta-substituted aryllead compounds generated by a halogen-boron-lead exchange sequence. The enolates of compounds 15, 19, and 25, each bearing all-carbon quaternary centers adjacent to the arylation site, failed to couple.

引用

页码：6885 / 6890

页数：6

共 40 条

[1] SYNTHESIS OF 2 USEFUL, ENANTIOMERICALLY PURE DERIVATIVES OF (S)-4-HYDROXY-2-CYCLOHEXENONE
AUDIA, JE
BOISVERT, L
PATTEN, AD
VILLALOBOS, A
DANISHEFSKY, SJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) : 3738 - 3740
[2] Synthetic studies on N-methylwelwitindolinone C isothiocyanate (welwistatin) and related substructures
Avendaño, C
Menéndez, JC
[J]. CURRENT ORGANIC SYNTHESIS, 2004, 1 (01) : 65 - 82
[3] Total synthesis of marine natural products without using protecting groups
Baran, Phil S.
Maimone, Thomas J.
Richter, Jeremy M.
[J]. NATURE, 2007, 446 (7134) : 404 - 408
[4] Enantioselective total syntheses of welwitindolinone A and fischerindoles I and G
Baran, PS
Richter, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) : 15394 - 15396
[5] Rapid access to the welwitindolinone alkaloid skeleton by cyclization of indolecarboxaldehyde substituted cyclohexanones
Baudoux, J
Blake, AJ
Simpkins, NS
[J]. ORGANIC LETTERS, 2005, 7 (19) : 4087 - 4089
[6] Rate enhancing ligands for lead(IV)-mediated arylations
Buston, JEH
Moloney, MG
Parry, AVL
Wood, P
[J]. TETRAHEDRON LETTERS, 2002, 43 (18) : 3407 - 3409
[7] Total synthesis of (±)-jiadifenin, a non-peptidyl neurotrophic modulator
Cho, YS
Carcache, DA
Tian, Y
Li, YM
Danishefsky, SJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (44) : 14358 - 14359
[8] DENG H, 2001, THESIS U CALIFORNIA
[9] Aryllead(IV) reagents in synthesis:: Formation of the C11 quaternary center of N-methylwelwitindolinone C isothiocyanate
Deng, HB
Konopelski, JP
[J]. ORGANIC LETTERS, 2001, 3 (19) : 3001 - 3004
[10] Catalytic asymmetric synthesis of all-carbon quaternary stereocenters
Douglas, CJ
Overman, LE
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5363 - 5367

← 1 2 3 4 →