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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)