Article
A synthetic approach to rocaglamide via reductive cyclization of š¯›æ-keto nitriles
The Journal of Organic Chemistry
Document Type
Article
Disciplines
Publication Version
Published Version
Publication Date
1-1-1989
DOI
10.1021/jo00262a022
Abstract
The anticancer agent rocaglamide contains a novel bicyclo[3.3.0]octanol structure. The approach to this molecule involved the preparation of a hydroxy ketone intermediate via a samarium-mediated cyclization. This ketone was then converted into an excellent Michael acceptor via novel chemistry. Subsequent steps led to the preparation of an isomer of rocaglamide. An X-ray determination supported our view that cuprate addition occurred with unusual concave selectivity.
Copyright Owner
American Chemical Society
Copyright Date
1989
Language
en
File Format
application/pdf
Citation Information
George A. Kraus and James O. Sy. "A synthetic approach to rocaglamide via reductive cyclization of š¯›æ-keto nitriles" The Journal of Organic Chemistry Vol. 54 Iss. 1 (1989) p. 77 - 83 Available at: http://works.bepress.com/george_kraus/33/
Reprinted (adapted) with permission from The Journal of Organic Chemistry, 54(1); 77-83. Doi: 10.1021/jo00262a022. Copyright 1989. American Chemical Society.