Work

Enantioselective total synthesis of decytospolide A and decytospolide B using an Achmatowicz reaction

Year: 2018

Type: article

Abstract: Enantioselective syntheses of decytospolide A and decytospolide B are described here. The current synthesis highlights an Achmatowicz rearrangement of an optically active furanyl alcohol followed by reduction of the resulting dihydropyranone hemiacetal with BF3·OEt2 and Et3SiH to provide the saturated tetrahydropyranyl alcohol directly. This reduction was investigated with a variety of other Lewis acids. The synthesis also features Noyori asymmetric transfer hydrogenation and Friedel-Crafts acylation. Overall, the synthesis provides ready access to the natural products and may be useful in the preparation of bioactive derivatives.

Source: Organic & Biomolecular Chemistry

DOI: 10.1039/c8ob01529e

Authors: Arun K. Ghosh, Hannah M. Simpson, Anne M. Veitschegger

Institution: Purdue University West Lafayette

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Purdue University, National Institutes of Health, National Institute of General Medical Sciences

Awards: G1728854080, DESIGN AND SYNTHESIS OF NONPEPTIDE PROTEASE INHIBITORS