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1,4‐Pentenyne as a Five‐Carbon Synthon for Efficient and Selective Syntheses of Natural Products Containing 2,4‐Dimethyl‐1‐penten‐1,5‐ylidene and Related Moieties by Means of Zr‐Catalyzed Carboalumination of Alkynes and Alkenes
Author(s) -
Zhu Gangguo,
Negishi Eiichi
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200701512
Subject(s) - synthon , enantioselective synthesis , catalysis , combinatorial chemistry , organic chemistry , materials science , chemistry
Two highly efficient protocols for enantioselective synthesis of 2,4‐dimethyl‐1‐penten‐1,5‐ylidene derivatives involve the combined use of the Zr‐catalyzed methylalumination of alkynes (ZMA) and the Zr‐catalyzed asymmetric carboalumination of alkenes (ZACA). The ZMA/ZACA protocol has been applied to the synthesis of a nafuredin intermediate 14 and a potential intermediate 18 for milbemycin β 3 , while the ZACA/ZMA protocol has been applied to the synthesis of a (−)‐bafilomycin A 1 intermediate 25 .