Asymmetric synthesis of a tricyclic core structure of the securinega alkaloids virosecurinine and allosecurinine

被引:26
作者
Kammler, R
Polborn, K
Wanner, KT
机构
[1] Univ Munich, Dept Pharm, D-81377 Munich, Germany
[2] Univ Munich, Dept Chem, D-81377 Munich, Germany
[3] Verla Pharm Arzneimittel, D-82327 Tutzing, Germany
关键词
virosecurinine; allosecurinine; alpha-amidoalkylation;
D O I
10.1016/S0040-4020(03)00406-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise asymmetric synthesis of tricyclic core structures of virosecurinine [(+)-1] and allosecurinine [(-)-2] is presented. An asymmetric electrophilic alpha-amidoalkylation reaction employing a chiral enamide gave access to enantiopure (S)-2-anisylpiperidine with the diastereoselectivity (d.s.) of 93/7. The latter was transformed into the target compounds, with the main steps involving a Birch-reduction followed by an ozonolysis of the resulting 1,4-cylohexadiene and a final spirocyclization reaction. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3359 / 3368
页数:10
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