Synthesis of Leprapinic Acid, Calycine and Analogues by Sequential “[3+2] Cyclization/Suzuki/Lactonization” Reactions | Zendy

Ahmed Zafar | Zendy; Albrecht Uwe | Zendy; Langer Peter | Zendy

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Synthesis of Leprapinic Acid, Calycine and Analogues by Sequential “[3+2] Cyclization/Suzuki/Lactonization” Reactions

Author(s) -

Ahmed Zafar,

Albrecht Uwe,

Langer Peter

Publication year - 2005

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.200500142

Subject(s) - chemistry , silyl enol ether , enol , silyl ether , ether , silylation , organic chemistry , enol ether , medicinal chemistry , catalysis

Calycine and analogues were prepared on the basis of Suzuki cross‐coupling reactions of γ‐alkylidene‐α‐hydroxybutenolides – readily available by cyclization of 1,3‐dicarbonyl dianions or 1,3‐bis(silyl enol ether)s with oxalyl derivatives – and subsequent boron tribromide‐mediated lactonization. Leprapinic acid was prepared by chemoselective boron tribromide‐mediated deprotection of permethylated leprapinic acid. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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