Use of biological systems for the preparation of chiral molecules. 3. Application in pheromone synthesis: preparation of sulcatol enantiomers

Both enantiomers of sulcatol, an aggregation pheromone, are prepared by microbial asymmetric reduction of prochiral 6-methylhept-5-en-2-one. Bacteria, yeast, fungi, and commercial enzymes which give high optical purities are used. Enzymatic resolution of (.+-.)-sulcatol by pig pancreatic lipase is c...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 52; no. 2; pp. 256 - 260
Main Authors Belan, Andre, Bolte, Jean, Fauve, Annie, Gourcy, Jean G, Veschambre, Henri
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.01.1987
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Online AccessGet full text

Cover

More Information
Summary:Both enantiomers of sulcatol, an aggregation pheromone, are prepared by microbial asymmetric reduction of prochiral 6-methylhept-5-en-2-one. Bacteria, yeast, fungi, and commercial enzymes which give high optical purities are used. Enzymatic resolution of (.+-.)-sulcatol by pig pancreatic lipase is carried out in anhydrous ether. The use of biological systems in organic chemistry to prepare chiral alcohols is discussed in terms of availability, cost, specific equipment, and chemical and optical yields.
Bibliography:ark:/67375/TPS-L30584BG-7
istex:26A3E1793416C49ACAB0CCC9E8007E946AF0B9BF
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00378a017