A Short Formal Synthesis of Squalamine from a Microbial Metabolite

200032 citationsJournal Article

Authors

William A. Kinney · Ash Stevens (United States)

Xuehai Zhang · University of Iowa

Jon I. Williams · University of Iowa

Sean Johnston · Ash Stevens (United States)

Ronald S. Michalak · University of Iowa

Milind Deshpande · Ash Stevens (United States)

Larry Dostal ·

Abstract

A short formal synthesis of squalamine is described, utilizing the biotransformation product 2, which is available in one step from commercially available 3-keto-23,24-bisnorchol-4-en-22-ol (1). Regioselective C-22 oxidation and C-24 sulfation of the corresponding alcohols in the presence of a free C-7 alcohol make for an efficient preparation of squalamine intermediate 11.

Topics & Keywords

Chemical synthesis and alkaloids Enzyme Catalysis and Immobilization Plant biochemistry and biosynthesis

Publication Details

Published in: Organic Letters

Volume 2, Issue 19, pp. 2921-2922

DOI: 10.1021/ol0059495

Field-Weighted Citation Impact: 2.43

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A Short Formal Synthesis of Squalamine from a Microbial Metabolite

Authors

Abstract

Topics & Keywords

Publication Details