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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Chiral Pool/Henry/Enzymatic Routes to Acetogenin Synthons

Author(s): Wesam S. Qayed and Frederick A. Luzzio

Volume 12, Issue 9, 2015

Page: [622 - 630] Pages: 9

DOI: 10.2174/1570178612666150819194241

Price: $65

Abstract

Enantiospecific and enantioselective approaches to the natural (16R,19R)- and the unnatural (16S,19S)- THF core of the bioactive acetogenin annonacin are described which utilizes both a chiral pool synthesis and enzymatic transformations. In the antipodal (2S,5S) THF series derived from D- (+)-glucosamine, the semi-protected THF aldehyde synthon allows for two-directional synthetic elaboration through a Henry reaction with a lipid-like nitroalkane. The resulting nitroalcohol having the unnatural (2S,5S)-THF core was oxidized to the corresponding -nitroketone using a modified Collins oxidation. The intermediate -nitroketone has potential for the preparation of the C15-C32 core and analogues through subsequent removal of the nitro group and reduction of the carbonyl.

Keywords: Acetogenins, angiogenesis, THF’s, lipases, chiral pool, Henry reaction.

Graphical Abstract

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