Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

1-1989

Journal or Book Title

The Journal of Organic Chemistry

Volume

54

Issue

1

First Page

77

Last Page

83

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.

Comments

Reprinted (adapted) with permission from The Journal of Organic Chemistry, 54(1); 77-83. Doi: 10.1021/jo00262a022. Copyright 1989. American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

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