Total synthesis of (+)-zaragozic acid C

被引：47

作者：

Armstrong, A ^{[1
]}

Barsanti, PA ^{[1
]}

Jones, LH ^{[1
]}

Ahmed, G ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 21期

关键词：

D O I：

10.1021/jo000700m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of (+)-zaragozic acid C is described. Key features of the synthesis are the use of a double Sharpless asymmetric dihydroxylation reaction of diene 6 to control stereochemistry at four contiguous stereocenters from C3 to C6; the introduction of the C1-side chain by reaction between the anion derived from the dithiane monosulfoxide 27 and the core aldehyde 12; a high yielding, acid-mediated simultaneous acetonide deprotection-dithiane removal-ketalization procedure leading exclusively to the 2,8-dioxabicyclo[3.2.1]octane core 34; and a novel triple oxidation procedure allowing installation of the tricarboxylic acid.

引用

页码：7020 / 7032

页数：13

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