Optically pure gamma-butyrolactones and epoxy esters via two stereocentered HKR of 3-substituted epoxy esters: a formal synthesis of (-)-paroxetine, Ro 67-8867 and (+)-eldanolide

TitleOptically pure gamma-butyrolactones and epoxy esters via two stereocentered HKR of 3-substituted epoxy esters: a formal synthesis of (-)-paroxetine, Ro 67-8867 and (+)-eldanolide
Publication TypeJournal Article
Year of Publication2013
AuthorsDevalankar, DA, Karabal, PU, Sudalai, A
JournalOrganic & Biomolecular Chemistry
Volume11
Issue8
Pagination1280-1285
Date PublishedJAN
ISSN1477-0520
Abstract

The HKR of racemic anti- or syn-3-substituted epoxy esters catalyzed by a Co(III)salen complex provides ready access to the corresponding enantioenriched 3,4-disubstituted gamma-butyrolactones and 3-substituted epoxy esters. This strategy has been successfully employed in the formal synthesis of biologically active 3,4-disubstituted piperidine derivatives, (-)-paroxetine and Ro 67-8867 and a natural product, (+)-eldanolide.

DOI10.1039/c3ob27321k
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)3.487
Divison category: 
Chemical Engineering & Process Development