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Pot and time economies in the total synthesis of Corey lactone

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Abstract

The Corey lactone is a highly versatile intermediate for the synthesis of a variety of prostaglandin hormones that natively control a multitude of important physiological processes. Starting from commercially available compounds, we herein disclose a time-economical, one-pot enantioselective preparation of the Corey lactone by virtue of a new diphenylprolinol silyl ether-mediated domino Michael/Michael reaction to afford the substituted cyclopentanone core in a formal (3 + 2) cycloadditive fashion. More broadly, this work advances the on-demand, gram-scale synthesis of high-value targets involving chemically orthogonal transformations, whereby distinct reactions of acids, bases, organometalics, reductants and oxidants can be carried out in a single reaction vessel in a sequential fashion.

Graphical abstract: Pot and time economies in the total synthesis of Corey lactone

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Article information


Submitted
16 Nov 2019
Accepted
20 Dec 2019
First published
23 Dec 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Pot and time economies in the total synthesis of Corey lactone

N. Umekubo, Y. Suga and Y. Hayashi, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC05824A

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