Synthesis of (-)-β conhydrine and analogues using N-Boc-2-acyl oxazolidine methodology and ring closing metathesis

被引：43

作者：

Agami, C ^{[1
]}

Couty, F ^{[1
]}

Rabasso, N ^{[1
]}

机构：

[1] Univ Paris 06, Associe CNRS, Lab Synthese Asymetr, F-75005 Paris, France

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 21期

关键词：

oxazolidines; asymmetric synthesis; ring closing metathesis;

D O I：

10.1016/S0040-4039(00)00580-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two key-steps involving: (i) a stereoselective reduction of an N-Boc-2-acyl oxazolidine; and (ii) an RCM performed on enantiopure trans-3,4,5-trisubstituted oxazolidin-2-ones account for the synthesis of unsaturated bicyclic oxazolidin-2-ones with various sizes of ring. One of these bicyclic compounds was transformed into (-)-beta-conhydrin. An unsaturated and a dihydroxylated analogue of this alcaloid were also prepared from the same starting material. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4113 / 4116

页数：4

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