Chiral Pool/Henry/Enzymatic Routes to Acetogenin Synthons

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

Journal Name: Letters in Organic Chemistry

Volume 12 , Issue 9 , 2015

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Graphical 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.

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Article Details

Year: 2015
Page: [622 - 630]
Pages: 9
DOI: 10.2174/1570178612666150819194241
Price: $58

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