Oxabicyclo[3.2.1]octenes in organic synthesis: Direct ring opening of oxabicyclo[3.2.1] ring systems with diisobutylaluminum hydride and a silyl ketene acetal-synthesis of the chiral C(19)-C(26) and C(27)-C(32) fragments of scytophycin C

被引：20

作者：

Hunt, KW ^{[1
]}

Grieco, PA ^{[1
]}

机构：

[1] Montana State Univ, Dept Chem & Biochem, Bozeman, MT 59717 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 02期

关键词：

D O I：

10.1021/ol010253c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

GRAPHICS An efficient strategy for transforming meso-oxabicyclo[3.2.1]octenone 1 into optically active intermediates for macrolide synthesis has been developed. The direct bridgehead opening of optically active oxabicyclo[3.2.1]octene derivative 2 with hydride or a silyl ketene acetal utilizing the highly polar medium lithium perchlorate in diethyl ether resulted in highly functionalized cycloheptenones, which were transformed into the C(19)-C(26) and C(27)-C(32) fragments of Scytophycin C.

引用

页码：245 / 248

页数：4

共 23 条

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