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Formal Syntheses of (±)‐Methylenomycins A and B
Author(s) -
Hong FangTsao,
Lee KungShing,
Liao ChunChen
Publication year - 2000
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200000008
Subject(s) - chemistry , cyclopentenone , methanol , stereochemistry , organic chemistry
The syntheses of methyl ester of (±)‐desepoxy‐4,5‐didehydromethylenomycin A ( 4 ) and 2,3‐dimethyl‐5‐methoxycarbonyl‐2‐cyclopentenone ( 5 ) were accomplished from a common starting material, 2,3‐dimethyl‐4‐methoxyphenol (8), in only four and two steps in 35% and 53% overall yields, respectively. Photochemical rearrangements of masked p ‐benzoquinones in methanol are the key steps.