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Issue 8, 2013
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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

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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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Publication details

The article was received on 29 Nov 2012, accepted on 04 Jan 2013 and first published on 08 Jan 2013


Article type: Communication
DOI: 10.1039/C3OB27321K
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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