Enantioselective total syntheses of omuralide, 7-epi-omuralide, and (+)-lactacystin

被引：52

作者：

Hayes, Christopher J. ^{[1
]}

Sherlock, Alexandra E. ^{[1
]}

Green, Martin P. ^{[1
]}

Wilson, Claire ^{[1
]}

Blake, Alexander J. ^{[1
]}

Selby, Matthew D. ^{[2
]}

Prodger, Jeremy C. ^{[3
]}

机构：

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

[2] Pfizer Global Res & Dev, Sandwich CT13 9NJ, Kent, England

[3] GlaxoSmithKline Inc, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 06期

关键词：

D O I：

10.1021/jo7027695

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An alkylidene carbene 1,5-CH insertion has been used as a key step in an enantioselective total syntheses of omuralide, its C7-epimer, and (+)-lactacystin. An additional noteworthy feature of the synthesis is the use of a novel oxidative deprotection procedure, utilizing DMDO, for the conversion of a late-stage benzylidene acetal into a primary alcohol and a secondary benzoate ester.

引用

页码：2041 / 2051

页数：11

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