Concise synthesis of 4-acylamino analogues of 2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acids (LY354740) from an acylnitroso Diels-Alder cycloadduct

被引：32

作者：

Lee, WL ^{[1
]}

Miller, MJ ^{[1
]}

机构：

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 13期

关键词：

D O I：

10.1021/jo0495034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Concise total syntheses of 4-acylamino analogues of LY354740 were accomplished employing an N-Boc acylnitroso Diels-Alder cycloadduct as the starting material. The syntheses involved N-O bond cleavage, oxidation, intermolecular cyclopropanation, Bucherer-Bergs reaction, hydrolysis, and regioselective acylation with a temporary copper chelate. The synthesis of an optically active compound was also achieved.

引用

页码：4516 / 4519

页数：4

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