Toward the second-generation synthesis of zaragozic acids:: Construction of the 2,8-dioxabicyclo[3.2.1]octane core system via tandem carbonyl ylide formation and 1,3-dipolar cycloaddition sequence

被引：52

作者：

Kataoka, O

Kitagaki, S

Watanabe, N

Kobayashi, J

Nakamura, S

Shiro, M

Hashimoto, S ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 060, Japan

[2] Rigaku Corp, Akishima, Tokyo 196, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 16期

关键词：

D O I：

10.1016/S0040-4039(98)00203-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient construction of the 2,8-dioxabicyclo[3.2.1]octane core structure of zaragozic acids, inhibitors of the enzyme squalene synthase, has been achieved by exploiting the sequence of rhodium(II)-mediated intramolecular carbonyl ylide formation from an alpha-diazo ester and stereocontrolled 1,3-dipolar cycloaddition with (E)-3-hexene-2,5-dione. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2371 / 2374

页数：4

共 26 条

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Biller SA, 1996, CURR PHARM DESIGN, V2, P1

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