Skip to main content

Alcohol Dehydrogenase‐Catalyzed Synthesis of Enantiomerically Pure

Buy Article:

$51.00 plus tax (Refund Policy)

Abstract:

Abstract

Starting from ethyl 4‐bromobutyrate, the chemoenzymatic synthesis of 6‐vinyl‐tetrahydro‐pyran‐2‐one has been accomplished. A screening of a number of available alcohol dehydrogenases and intense optimization of reaction parameters enabled us to establish an efficient synthesis of either enantiomer of the vinyllactone with excellent enantiomeric excess (>99%). The scope of possible applications of enantiopure vinyllactones has been verified by subjection to cross‐metathesis resulting in the total synthesis of the insect pheromone (S)‐5‐hexadecanolide and the cytotoxic styryllactone goniothalamine as well as derivatives thereof.

Document Type: Research Article

DOI: http://dx.doi.org/10.1002/adsc.201200258

Affiliations: Institut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Stetternicher Forst Geb. 15.8, 52426 Jülich, Germany, Fax: (+49)-2461-616196

Publication date: September 17, 2012

bpl/adsc/2012/00000354/00000013/art00026
dcterms_title,dcterms_description,pub_keyword
6
5
20
40
5

Access Key

Free Content
Free content
New Content
New content
Open Access Content
Open access content
Subscribed Content
Subscribed content
Free Trial Content
Free trial content
Cookie Policy
X
Cookie Policy
Ingenta Connect website makes use of cookies so as to keep track of data that you have filled in. I am Happy with this Find out more