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Regio‐ and Stereoselective Synthesis of γ ‐Alkylidenebutenolides by Cyclization of Dilithiated 1,3‐Dicarbonyl Compounds with N , N ′‐Dimethoxy‐ N , N ′‐dimethylethane‐ diamide
Author(s) -
Langer Peter,
Stoll Martin
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990614)38:12<1803::aid-anie1803>3.0.co;2-5
Subject(s) - stereoselectivity , chemistry , natural product , stereochemistry , organic chemistry , catalysis
The remarkably simple synthesis of γ ‐alkylidenebutenolides 3 is achieved by cyclization of the dilithiated 1,3‐dicarbonyl compounds 1 with N , N ′‐dimethoxy‐ N , N ′‐dimethylethanediamide ( 2 ). This regio‐ and stereoselective cyclization provides a route to a wide range of butenolides, which are of pharmacological relevance and of importance for natural product synthesis.