Systematic construction of a monotetrahydrofuran-ring library in annonaceous acetogenins by asymmetric alkynylation and stereodivergent tetrahydrofuran-ring formation

被引：46

作者：

Kojima, N ^{[1
]}

Maezaki, N ^{[1
]}

Tominaga, H ^{[1
]}

Asai, M ^{[1
]}

Yanai, M ^{[1
]}

Tanaka, T ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2003年 / 9卷 / 20期

关键词：

alkynylations; cyclization; polyketides; stereodivergent synthesis; synthetic methods;

D O I：

10.1002/chem.200305185

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

All eight diastereoisomers of the monotetrahydrofuran-ring cores of annonaceous acetogenins have been synthesized through utilization of asymmetric alkynylation and stereodivergent one-pot tetrahydrofuran-ring formation. In all cases, the asymmetric alkynylation proceeded with very high diastereoselectivity to give eight kinds of optically pure tetrahydrofuran core from a common alpha-oxyaldehyde. We also describe a comparison of the H-1 NMR, C-13 NMR, and CD spectral data of the eight isomers and give full details of the tetrahydrofuran-ring construction including a model study of asymmetric alkynylation.

引用

页码：4980 / 4990

页数：11

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