Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

11-1980

Journal or Book Title

The Journal of Organic Chemistry

Volume

45

Issue

24

First Page

4820

Last Page

4825

DOI

10.1021/jo01312a003

Abstract

A synthetic route to the AB ring system of verrucarol is described. After two routes employing intramolecular cyclization failed, the Diels-Alder reaction of methyl coumalate and isoprene afforded bicyclic lactone 13. Transformation of 13 into hydroxy lactone 16 involved cuprate addition, hydroxylation, and oxidation. The conversion of 16 into desired keto alcohol 14 was accomplished by enol ether formation, reduction of the lactone and ester, and hydrolysis of the enol ether. The successful nine-step sequence proceeded in an overall yield of 7.9% from methyl coumalate.

Comments

Reprinted (adapted) with permission from The Journal of Organic Chemistry, 45(24); 4820-4825. Doi: 10.1021/jo01312a003. Copyright 1980 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

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