Synthesis of (+)- and (-)-Geissman-Waiss lactone from chiral sulfonium salts

被引：4

作者：

Lopez-Gonzalez, Ricardo ^{[1
]}

Gnecco, Dino ^{[1
]}

Juarez, Jorge R. ^{[1
]}

Orea, Maria L. ^{[1
]}

Gomez-Calvario, Victor ^{[1
]}

Bernes, Sylvain ^{[2
]}

Aparicio, David M. ^{[1
]}

Teran, Joel L. ^{[1
]}

机构：

[1] Benemerita Univ Autonoma Puebla, Ctr Quim, Inst Ciencias, Edif IC9,Complejo Ciencias,CU, Puebla 72570, Mexico

[2] Benemerita Univ Autonoma Puebla, Inst Fis, Edif IF2,Lab 104,CU, Puebla 72570, Mexico

来源：

TETRAHEDRON LETTERS | 2020年 / 61卷 / 13期

关键词：

Cyclic zwitterion; Pyrrolidinone; Enantio specific; Geissman-Waiss lactone; GEISSMAN-WAISS LACTONE; ENANTIOSELECTIVE SYNTHESIS; PYRROLIZIDINE ALKALOIDS; METABOLIC-ACTIVATION; (+)-RETRONECINE;

D O I：

10.1016/j.tetlet.2020.151697

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel series of chiral cyclic zwitterionic pyrrolidinone type intermediates was prepared via regioselective 5-exo-trig-ring-closure of the corresponding chiral sulfonium salts. This synthetic strategy allowed the rapid non-racemic synthesis of the Geissman-Waiss lactone in six steps and 35% overall yield. (C) 2020 Elsevier Ltd. All rights reserved.

引用

页数：4

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