β-hydroxy-γ-lactones as chiral building blocks for the enantioselective synthesis of marine natural products

被引：66

作者：

García, C ^{[1
]}

Martín, T ^{[1
]}

Martín, VS ^{[1
]}

机构：

[1] Univ La Laguna, Inst Bioorgan Antonio Gonzalez, E-38206 Tenerife, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 04期

关键词：

D O I：

10.1021/jo0057194

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of trans-(+)-laurediol, (2S,3S,5R)-5-[(1R)-1-hydroxy-9-decenyl]-2-pentyltetrahydro-3-furanol, and (2S,3S,5S)-5-[(1S)-1-hydroxy-9-decenyl]-2-pentyltetrahydro-3-furanol are described. In addition, a formal synthesis of trans-(-)-kumausyne is also developed. All the synthetic procedures have in common the use of enantiomerically enriched beta -hydroxy-gamma -lactones, easily available by Sharpless asymmetric dihydroxylation (AD) from the suitable beta,gamma -unsaturated ester. The use of Katsuki-Sharpless asymmetric epoxidation (AE) as an additional enantioselective reaction provides cyclic compounds of high enantiomeric purity.

引用

页码：1420 / 1428

页数：9

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