Chiral Pool/Henry/Enzymatic Routes to Acetogenin Synthons

Title:Chiral Pool/Henry/Enzymatic Routes to Acetogenin Synthons

Volume: 12 Issue: 9

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

Affiliation:

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

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.

Cite this article as:

Qayed S. Wesam and Luzzio A. Frederick, Chiral Pool/Henry/Enzymatic Routes to Acetogenin Synthons, Letters in Organic Chemistry 2015; 12 (9) . https://dx.doi.org/10.2174/1570178612666150819194241