- Chiral Pool/Henry/Enzymatic routes to acetogenin synthons
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Enantio specific and enantioselective approaches to the natural (16 R,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 a-nitroketone using a modified Collins oxidation. The intermediate a-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.
- Qayed, Wesam S.,Luzzio, Frederick A.
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p. 622 - 630
(2015/11/09)
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