Total synthesis of (-)-desoxoprosopinine via the diastereoselective reduction of homochiral2-acyl-N-Boc-oxazolidines

被引：40

作者：

Agami, C ^{[1
]}

Couty, F ^{[1
]}

Mathieu, H ^{[1
]}

机构：

[1] Univ Pierre & Marie Curie, CNRS, Lab Synth Asymetr, F-75005 Paris, France

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 21期

关键词：

oxazolidines; alkaloids; asymmetric synthesis;

D O I：

10.1016/S0040-4039(98)00646-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(-)-Desoxoprosopinine was synthesised from (R)-phenylglycinol as the chiral source. The three distinct steps used for the construction of the three stereogenic centers of the target were all highly diastereoselective. These steps include a reduction of a homochiral N-Boc-2-acyl oxazolidine and the stereoselectivity of this reaction can be explained by a non chelated model. An original N-debenzylation of the phenyl glycinol appendage was devised in this synthesis. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：3505 / 3508

页数：4

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