Conjugate additions to phenylglycinol-derived unsaturated δ-lactams.: Enantioselective synthesis of uleine alkaloids

被引：62

作者：

Amat, M ^{[1
]}

Pérez, M

Llor, N

Escolano, C

Luque, FJ

Molins, E

Bosch, J

机构：

[1] Univ Barcelona, Fac Pharm, Lab Organ Chem, Barcelona 08028, Spain

[2] Univ Barcelona, Fac Pharm, Dept Phys Chem, Barcelona 08028, Spain

[3] CSIC, Inst Ciencia Mat, Cerdanyola Del Valles, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 25期

关键词：

D O I：

10.1021/jo0487101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereochemical outcome of the conjugate addition of a variety of stabilized nucleophiles (2-indoleacetic enolates and sulfur-stabilized anions) to the phenylglycinol-derived unsaturated lactams trans-2, cis-2, and its 8-ethyl-substituted analogue 10 is studied. The factors governing the exo or endo facial stereos electivity are discussed. This methodology provides short synthetic routes to either cis- or trans-3,4-disubstituted enantiopure piperidines as well as efficient routes for the enantioselective construction of the tetracyclic ring system of uleine alkaloids, both in the normal and 20-epi series. The formal total synthesis of several alkaloids of this group is reported.

引用

页码：8681 / 8693

页数：13

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