Total synthesis of (-+)-dysidiolide

被引：23

作者：

Demeke, D ^{[1
]}

Forsyth, CJ ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

来源：

TETRAHEDRON | 2002年 / 58卷 / 32期

关键词：

total synthesis; ((+)(-))-dysidiolide; intramolecular stereoinduction;

D O I：

10.1016/S0040-4020(02)00663-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of (+/-)-dysidiolide was accomplished with a high level of intramolecular stereo-induction. Methylation of 6-carboethoxy-3-chloro-5-methyl-cyclohex-2-enone provided 33 bearing the 6,7-trans-dimethyl substitution of the C6-C11 B-ring. Diastereoselective conjugate addition upon enone 34 installed the C11 stereogenic center. Annulation then provided an A-ring enone (23), a substrate for a challenging conjugate addition of the branched pentenyl side chain, The combination of tri-n-butylphosphine. boron trifluoride etherate, and a dialkylcuprate uniquely effected conjugate addition to yield 58. Incorporation of the hydroxybutenolide-containing side chain completed the total synthesis and established the viability of a general approach for the preparation of the isolabdanoid terpene system. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：6531 / 6544

页数：14

共 40 条

[1] Dysidiolide and related γ-hydroxy butenolide compounds as inhibitors of the protein tyrosine phosphatase, Cdc25 [J].