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The sherry‐lactones and solerone. Their identification in dried figs
Author(s) -
Näf R.,
Jaquier A.,
Boschung A. F.,
Lindström M.
Publication year - 1995
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.2730100404
Subject(s) - diastereomer , chemistry , ketone , enantiomer , stereochemistry , dihydroxylation , lactone , enantiomeric excess , sharpless asymmetric dihydroxylation , organic chemistry , enantioselective synthesis , catalysis
The two diastereoisomers of sherry‐lactone (5‐hydroxy‐4‐hexanolide, 1 and 2) and the corresponding ketone (5‐keto‐4‐hexanolide = solerone, 3) were identified in a solvent extract of dried figs and their enantiomeric distributions were determined. The (4S,5S)‐ and the (4R,5R)‐enantiomers of diastereoisomer 1 were selectively synthesized following the method of Sharpless (asymmetric dihydroxylation) and their optical rotations were measured. Diastereoisomer 2 was isolated as an almost racemized by‐product. Racemic ketone 3 was obtained by oxidation of either (4S,5S)‐ or (4R,5R)‐1.