A concise and stereoselective synthesis of the A-ring fragment of the gambieric acids

被引：61

作者：

Clark, JS ^{[1
]}

Fessard, TC ^{[1
]}

Wilson, C ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 11期

关键词：

D O I：

10.1021/ol049483s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The A-ring fragment of the gambieric acids has been prepared by a short and efficient route. The key 3(2H)-furanone intermediate has been obtained by [2,3] rearrangement of an allylic oxonium ylide generated from intramolecular reaction of a crotyl ether with a copper carbenoid. A single stereogenic center has been set by using a chiral pool starting material and the other three have been established by using highly diastereoselective substrate-controlled transformations.

引用

页码：1773 / 1776

页数：4

共 29 条

[1] Stereoselective synthesis of the antifungal GM222712
Bueno, JM
Coterón, JM
Chiara, JL
Fernández-Mayoralas, A
Fiandor, JM
Valle, N
[J]. TETRAHEDRON LETTERS, 2000, 41 (22) : 4379 - 4382
[2] Stereoselective synthesis of tetrahydropyran-3-ones by rearrangement of oxonium ylides generated from metal carbenoids
Clark, JS
Whitlock, G
Jiang, S
Onyia, N
[J]. CHEMICAL COMMUNICATIONS, 2003, (20) : 2578 - 2579
[3] Clark JS, 1999, CHEM COMMUN, P749
[4] A novel approach to the construction of medium-ring carbocycles utilising the rearrangement of oxonium ylides generated from metal carbenoids
Clark, JS
Bate, AL
Grinter, T
[J]. CHEMICAL COMMUNICATIONS, 2001, (05) : 459 - 460
[5] SYNTHESIS OF CYCLIC ETHERS FROM COPPER CARBENOIDS BY FORMATION AND REARRANGEMENT OF OXONIUM YLIDES
CLARK, JS
KROWIAK, SA
STREET, LJ
[J]. TETRAHEDRON LETTERS, 1993, 34 (27) : 4385 - 4388
[6] Stereoselective synthesis of the bicyclic core structure of the highly oxidised sesquiterpene neoliacinic acid
Clark, JS
Dossetter, AG
Whittingham, WG
[J]. TETRAHEDRON LETTERS, 1996, 37 (31) : 5605 - 5608
[7] A SHORT SYNTHESIS OF (+/-)-DECARESTRICTINE-L
CLARK, JS
WHITLOCK, GA
[J]. TETRAHEDRON LETTERS, 1994, 35 (34) : 6381 - 6382
[8] DIASTEREOSELECTIVE SYNTHESIS OF 2,5-DIALKYL TETRAHYDROFURAN-3-ONES BY A COPPER-CATALYZED TANDEM CARBENOID INSERTION AND YLIDE REARRANGEMENT REACTION
CLARK, JS
[J]. TETRAHEDRON LETTERS, 1992, 33 (41) : 6193 - 6196
[9] Doyle M. P., 1998, MODERN CATALYTIC MET, P355
[10] Kadota I, 2001, TETRAHEDRON LETT, V42, P3645, DOI 10.1016/S0040-4039(01)00529-9

← 1 2 3 →