Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

12-1978

Journal or Book Title

The Journal of Organic Chemistry

Volume

43

Issue

26

First Page

4923

Last Page

4924

DOI

10.1021/jo00420a004

Abstract

An efficient synthesis of 9-deoxykalafungin (lb) in six steps from readily available starting materials is described. The key step, in which all of the carbon atoms present in the target molecule are assembled, is the addition of 2-tert-butoxyfuran to 2-acetyl-l,4-naphthoquinone. Hydride reduction, followed by removal of the tert-butyl protecting group and addition of the C-1 alcohol to the unmasked hutenolide, affords intermediate 13, which can be oxidized with argentic oxide to lb in 17% overall yield.

Comments

Reprinted (adapted) with permission from The Journal of Organic Chemistry, 43(26); 4923-4924. Doi: 10.1021/jo00420a004. Copyright 1978 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

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