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Synthetic Microbial Chemistry, XXV. Synthesis of the Enantiomers of Differolide [4‐(2′,5′‐Dihydro‐2′‐oxo‐3′‐furanyl)‐3a,4,5,6‐tetrahydro‐1(3 H )‐isobenzofuranone], a Microbial Bioregulator for the Formation of Aerial Mycelium and Spores of Streptomyces glaucescens
Author(s) -
Mori Kenji,
Tomioka Hiroki,
Fukuyo Emiko,
Yanagi Kazunori
Publication year - 1993
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.1993199301109
Subject(s) - chemistry , enantiomer , stereochemistry , environmental chemistry
Both the enantiomers of differolide [4‐(2′,5′‐dihydro‐2′‐oxo‐3′‐furanyl)‐3a,4,5,6‐tetrahydro‐1(3 H )‐isobenzofuranone ( 1 )] were synthesized by starting from the known lactone rac ‐ 2 . The key step was the optical resolution of hemiacetal rac ‐ 3 by acetal formation with (+)‐ or (−)‐menthol. A single crystal X‐ray analysis of acetal (−)‐ 4a established its absolute configuration. Since the natural product was known to be racemic, the present synthesis of both (+)‐ and (−)‐ 1 with known absolute configuration provided molecular probes to examine the enantioselectivity at the receptor site of Streptomyces glaucescens .