SYNTHESIS OF OPTICALLY-ACTIVE T-BUTYL (3R,5S)-3,5-ISOPROPYLIDENEDIOXY-6-HEPTYNOATE THROUGH BAKERS-YEAST REDUCTION OF METHYL 3-OXO-4-PENTYNOATE

Authors
ANSARI MH KUSUMOTO T HIYAMA T
Citation
Mh. Ansari et al., SYNTHESIS OF OPTICALLY-ACTIVE T-BUTYL (3R,5S)-3,5-ISOPROPYLIDENEDIOXY-6-HEPTYNOATE THROUGH BAKERS-YEAST REDUCTION OF METHYL 3-OXO-4-PENTYNOATE, Tetrahedron letters, 34(51), 1993, pp. 8271-8274
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
51
Year of publication
1993
Pages
8271 - 8274
Database
ISI
SICI code
0040-4039(1993)34:51<8271:SOOT(>2.0.ZU;2-A
Abstract
Baker's yeast reduction of methyl 3-oxo-4-pentynoate gave the correspo nding (S)-3-hydroxy ester (80% e.e.), whereas its 5-trimethylsilyl der ivative gave the (R)-enantiomer (82% e.e.). The (S)-alcohol was led to optically active t-butyl (3R,5S)-3,5-isopropylidenedioxy-6-heptynoate , a versatile synthetic intermediate of artificial HMG-CoA reductase i nhibitors.