Terpestacin core structure. Control of stereochemistry

被引：17

作者：

Berger, GO

Tius, MA

机构：

[1] Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA

[2] Canc Res Ctr Hawaii, Honolulu, HI 96813 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 22期

关键词：

D O I：

10.1021/ol052015d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The alpha-hydroxycyclopentenone core structure of terpestacin has been prepared in a model system through an allene ether Nazarov cyclization of an alkylidene-gamma-butyrolactone followed by regio- and stereoselective alkylation reactions. The stereochemistry at C15 (terpestacin numbering) has been used to control stereochemistry at C1 and at C23. The use of E-alkylidene-gamma-butyrolactones extends the scope of the cationic cyclopentannelation reaction.

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页码：5011 / 5013

页数：3

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