Premium
Synthesis of γ‐Alkylidenebutenolides by Formal [3+2] Cyclizations of 1,5‐ and 2,4‐Bis(trimethylsilyloxy)‐1,3,5‐hexatrienes with Oxalyl Chloride
Author(s) -
Freifeld Ilia,
Bose Gopal,
Eckardt Tobias,
Langer Peter
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600398
Subject(s) - oxalyl chloride , chemistry , butenolide , formal synthesis , chloride , organic chemistry , lewis acids and bases , medicinal chemistry , stereochemistry , catalysis
Lewis acid‐catalyzed cyclizations of 1,5‐bis(trimethylsilyloxy)‐1,3,5‐hexatrienes and 1,3,5‐tris(trimethylsilyloxy)‐1,3,5‐hexatrienes with oxalyl chloride resulted in the formation of polyunsaturated γ‐alkylidenebutenolides, while the cyclization of a 2,4‐bis(trimethylsilyloxy)‐1,3,5‐hexatriene with oxalyl chloride afforded a γ‐(2‐oxobut‐3‐en‐1‐ylidene)butenolide, permitting a formal synthesis of the natural product lucidone. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)