Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

10-1987

Journal or Book Title

The Journal of Organic Chemistry

Volume

52

Issue

22

First Page

4841

Last Page

4846

DOI

10.1021/jo00231a003

Abstract

11-Deoxydaunomycinone (6), ita 4-deoxy analogue 5, and 1-methoxy-4,ll-dideoxyduanomycinone were prepared by a sequence involving an intramolecular acyl transfer reaction followed by a tandem Claisen-Diels-Alder reaction. The resulting diketone could be oxidized to naphthoquinone 11 with DDQ. This quinone was then treated with either 1-[ (trimethylsilyl)oxy]butadiene or l-methoxy-1,3-cyclohexadiene to provide adducts that could be transformed into 5 and 6. Unfortunately, the presence of the C-7 carbonyl group decreased the regioselectivity of 11 in Diels-Alder reactions.

Comments

Reprinted (adapted) with permission from The Journal of Organic Chemistry,52(22); 4841-4846. Doi: 10.1021/jo00231a003. Copyright 1987 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

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