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Synthetic microbial chemistry, XXIV. Synthesis of antibiotic 1233A, an inhibitor of cholesterol biosynthesis
Author(s) -
Mori Kenji,
Takahashi Yoshio
Publication year - 1991
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.1991199101183
Subject(s) - chemistry , antibiotics , biosynthesis , biochemistry , cholesterol , enzyme
A synthesis of 1233A [(2 E ,4 E ,7 R ,2′ R ,3′ R )‐11‐[3′‐(hydroxymethyl)‐4′‐oxo‐2′‐oxetanyl]‐3,5,7‐trimethyl‐2,4‐undecadienoic acid ( 1a )] was achieved by employing ( R )‐2‐hydroxymethyl‐3‐butenyl acetate ( 2a ) and ( R )‐citronellic acid ( 3 ) as chiral building blocks. The former was prepared by lipase‐mediated asymmetric hydrolysis of the corresponding diacetate.