Open AccessSynthesis of the C4-Epi-Lomaiviticin B Core Reveals Subtle Stereoelectronic Effects
Author(s) -
Amy S. Lee,
Matthew D. Shair
Publication year - 2013
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol400832r
Subject(s) - stereocenter , chemistry , stereoselectivity , furan , core (optical fiber) , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , materials science , composite material
An efficient synthesis of the C4-epi-lomaiviticin B core is reported. The synthesis features a diastereoselective anionic formal furan Diels-Alder reaction and a stereoselective oxidative enolate dimerization. During the investigation, subtle yet critical stereoelectronic effects imparted by the C4-stereocenter were observed.
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