Synthesis of γ??Alkylidenebutenolides by Formal [3+ 2] Cyclizations of 1, 5??and 2, 4??Bis (trimethylsilyloxy)??1, 3, 5??hexatrienes with Oxalyl Chloride

…, G Bose, T Eckardt, P Langer

Index: Freifeld, Ilia; Bose, Gopal; Eckardt, Tobias; Langer, Peter European Journal of Organic Chemistry, 2007 , # 2 p. 351 - 355

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Citation Number: 12

Abstract

Abstract 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- ...