Vallartanone B: Synthesis and related studies

被引：11

作者：

Arimoto, H ^{[1
]}

Yokoyama, R ^{[1
]}

Nakamura, K ^{[1
]}

Okumura, Y ^{[1
]}

Uemura, D ^{[1
]}

机构：

[1] KEIO UNIV, FAC SCI & TECHNOL, DEPT CHEM, YOKOHAMA, KANAGAWA 223, JAPAN

来源：

TETRAHEDRON | 1996年 / 52卷 / 44期

关键词：

D O I：

10.1016/0040-4020(96)00852-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of vallartanone B, a gamma-pyrone-containing polypropionate from the marine mollusc Siphonaria maum, is described. A gamma-pyrone moiety, which was constructed by PPh(3)-CCl4 cyclization of a beta-triketone, and a C1-C6 segment were joined by a Sn(OTf)(2) aldol reaction and converted to vallartanone B. This synthesis allows for revision of the stereochemistry at C8. A conformational analysis war, performed using PM3 to examine the proposed interpretation of its CD spectrum. Copyright (C) 1996 Elsevier Science Ltd.

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页码：13901 / 13908

页数：8

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