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Synthetic microbial chemistry, XXIII. Synthesis of optically active virginiae butanolides A, B, C, and D and other autoregulators from streptomycetes
Author(s) -
Mori Kenji,
Chiba Naoki
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199019900105
Subject(s) - chemistry , optically active , streptomyces , actinomycetales , stereochemistry , streptomycetaceae , organic chemistry , bacteria , biology , genetics
Optically active A‐factor ( 1 ), the factor from Streptomyces viridochromogenes ( 2 ), the factors from S. bikiniensis and S. cyaneofuscatus ( 3–5 ), and virginiae butanolides A ( 6 ), B ( 7 ), C ( 8 ), and D ( 9 ) were synthesized starting from ( S )‐(−)‐paraconic acid ( 10 ). The absolute configurations of virginiae butanolides A and C were deduced to be (2 S ,3 R ,1′ R ).