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

Freifeld Ilia | Zendy; Bose Gopal | Zendy; Eckardt Tobias | Zendy; Langer Peter | Zendy

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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)

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