Issue 8, 2013
From the journal:

Organic & Biomolecular Chemistry

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

Dattatray A. Devalankar,a   Pratibha U. Karabala  and  Arumugam Sudalai*a  

* Corresponding authors

a Chemical Engineering and Process Development Division, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India
E-mail: a.sudalai@ncl.res.in
Fax: +91-02025902676

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 γ-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.

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

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Article information

DOI
https://doi.org/10.1039/C3OB27321K
Article type
Communication
Submitted
29 Nov 2012
Accepted
04 Jan 2013
First published
08 Jan 2013

Org. Biomol. Chem., 2013,11, 1280-1285

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

D. A. Devalankar, P. U. Karabal and A. Sudalai, Org. Biomol. Chem., 2013, 11, 1280 DOI: 10.1039/C3OB27321K

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