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
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
收藏
页码:1773 / 1776
页数:4
相关论文
共 29 条
[1]   Stereoselective synthesis of the antifungal GM222712 [J].
Bueno, JM ;
Coterón, JM ;
Chiara, JL ;
Fernández-Mayoralas, A ;
Fiandor, JM ;
Valle, N .
TETRAHEDRON LETTERS, 2000, 41 (22) :4379-4382
[2]   Stereoselective synthesis of tetrahydropyran-3-ones by rearrangement of oxonium ylides generated from metal carbenoids [J].
Clark, JS ;
Whitlock, G ;
Jiang, S ;
Onyia, N .
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 [J].
Clark, JS ;
Bate, AL ;
Grinter, T .
CHEMICAL COMMUNICATIONS, 2001, (05) :459-460
[5]   SYNTHESIS OF CYCLIC ETHERS FROM COPPER CARBENOIDS BY FORMATION AND REARRANGEMENT OF OXONIUM YLIDES [J].
CLARK, JS ;
KROWIAK, SA ;
STREET, LJ .
TETRAHEDRON LETTERS, 1993, 34 (27) :4385-4388
[6]   Stereoselective synthesis of the bicyclic core structure of the highly oxidised sesquiterpene neoliacinic acid [J].
Clark, JS ;
Dossetter, AG ;
Whittingham, WG .
TETRAHEDRON LETTERS, 1996, 37 (31) :5605-5608
[7]   A SHORT SYNTHESIS OF (+/-)-DECARESTRICTINE-L [J].
CLARK, JS ;
WHITLOCK, GA .
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 [J].
CLARK, JS .
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