Work

The Chiron Approach to (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol, a Key Subunit of HIV-1 Protease Inhibitor Drug, Darunavir

Year: 2020

Type: article

Abstract: We describe an enantioselective synthesis of (3 R,3 aS,6 aR )-hexahydrofuro[2,3- b ]furan-3-ol which is a key subunit of darunavir, a widely used HIV-1 protease inhibitor drug for the treatment of HIV/AIDS patients. The synthesis was achieved in optically pure form utilizing commercially available sugar derivatives as the starting material. The key steps involve a highly stereoselective substrate-controlled hydrogenation, a Lewis acid catalyzed anomeric reduction of a 1,2- O -isopropylidene-protected glycofuranoside, and a Baeyer–Villiger oxidation of a tetrahydrofuranyl-2-aldehyde derivative. This optically active ligand alcohol was converted to darunavir efficiently.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.0c02396

Authors: Arun K. Ghosh, Shivaji B. Markad, William L. Robinson

Institution: Purdue University West Lafayette

Language: Hebrew

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

SDG: Good health and well-being

Open Access status: green

Funders: National Institutes of Health, National Institute of Allergy and Infectious Diseases