Furan-Derived Chiral Bicycloaziridino Lactone Synthon: Collective Syntheses of Oseltamivir Phosphate (Tamiflu), (S)-Pipecolic acid and its 3-Hydroxy Derivatives

Subhash P Chavan; Appasaheb L Kadam; Shrikrishna S Shinde; Rajesh G Gonnade

doi:10.1002/asia.201901523

Furan-Derived Chiral Bicycloaziridino Lactone Synthon: Collective Syntheses of Oseltamivir Phosphate (Tamiflu), (S)-Pipecolic acid and its 3-Hydroxy Derivatives

Chem Asian J. 2020 Feb 3;15(3):415-424. doi: 10.1002/asia.201901523. Epub 2020 Jan 20.

Authors

Subhash P Chavan^{1

2}, Appasaheb L Kadam^{1

2}, Shrikrishna S Shinde¹, Rajesh G Gonnade^{2

3}

Affiliations

¹ Division of Organic Chemistry, CSIR-National Chemical Laboratory, Pune, 411008, India.
² Academy of Scientific and Innovative Research (AcSIR), New Delhi, 110025, India.
³ Physical and Materials Chemistry Division, CSIR-National Chemical Laboratory, Pune, 411008, India.

PMID: 31794104
DOI: 10.1002/asia.201901523

Abstract

A unified synthetic strategy for oseltamivir phosphate (tamiflu), (S)-pipecolic acid, and its 3-hydroxy derivatives from furan derived common chiral bicycloaziridino lactone synthon is described here. Key features are the short (4-steps), enantiopure, and decagram-scale synthesis of common chiral synthon from furan and its first-ever application in the total synthesis of biologically active compounds by taking the advantages of high functionalization ability of chiral synthon.

Keywords: Aziridine synthon; Chiral auxiliary; Collective synthesis; Pipecolic acid; Tamiflu.