Electrooxidation based strategy towards the core 3-amino-6-hydroxy-azepan-2-one

被引：6

作者：

David, M ^{[1
]}

Dhimane, H ^{[1
]}

机构：

[1] Univ Paris 05, UMR 8601, Chim & Biochim Pharmacol & Toxicol Lab, F-75270 Paris 06, France

来源：

SYNLETT | 2004年 / 06期

关键词：

bengamides; diastereoselectivity; dihydroxylation; electrooxidation; osmium;

D O I：

10.1055/s-2004-820048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe a practical synthesis of protected (3S,6R)-6-hydroxy-cyclolysine derivatives starting from Cyclic L-lysine. Evaluation of the electrochemical oxidation of various protected amino-caprolactams allowed a regioselective electromethoxylation at the alpha-position to the lactam nitrogen. Formation of the corresponding enamide by elimination of methanol followed by a diastereoselective dihydroxylation. diacetylation and subsequent regioselective reduction afford the orthogonally protected (3S,6R)-3-amino-6-hydroxy-azepan-2-one.

引用

收藏

页码：1029 / 1033

页数：5

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