Total synthesis of coraxeniolide-A

被引:40
作者
Renneberg, D [1 ]
Pfander, H [1 ]
Leumann, CJ [1 ]
机构
[1] Univ Bern, Dept Chem & Biochem, CH-3012 Bern, Switzerland
关键词
D O I
10.1021/jo005582h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of optically active coraxeniolide-A (la) and 4-epi-coraxeniolide-A (1b) is described. The approach is highly stereoselective and flexible in the preparation of a wide variety of members of the xeniolide family. The use of the Grob-fragmentation was pivotal for the stereospecific elaboration of the nine-membered ring. Coraxeniolide-A (la) was synthesized in 28 steps by using the Hajos-Parrish diketone 2 as starting material which is available enantiomerically pure.
引用
收藏
页码:9069 / 9079
页数:11
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