Pot and time economies in the total synthesis of Corey lactone.

Chemical Science
Nariyoshi UmekuboYujiro Hayashi

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.

References

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Feb 14, 2013·Angewandte Chemie·Yujiro Hayashi, Shigenobu Umemiya
Apr 21, 2017·Nature·Jacob T EdwardsPhil S Baran
Jul 25, 2017·Organic & Biomolecular Chemistry·Haihui Peng, Fen-Er Chen
Jul 28, 2017·Angewandte Chemie·Yujiro HayashiEunsang Kwon
Feb 1, 2016·Chemical Science·Yujiro Hayashi
Apr 1, 2018·Chemistry : a European Journal·Genki KawauchiYujiro Hayashi

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Citations

Apr 3, 2020·Organic & Biomolecular Chemistry·Dimitris KalaitzakisGeorgios Vassilikogiannakis
Jul 17, 2020·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Steven H BennettVarinder K Aggarwal
May 29, 2021·Nature Chemistry·Fuhao ZhangXumu Zhang
Feb 10, 2021·International Journal of Molecular Sciences·Constantin TănaseRaluca Elena Tănase
Feb 23, 2021·Accounts of Chemical Research·Yujiro Hayashi
Mar 29, 2020·Organic Letters·Roman KučeraStephen P Fletcher
Nov 25, 2020·Organic Letters·Nariyoshi Umekubo, Yujiro Hayashi
Dec 29, 2020·Journal of the American Chemical Society·Keitaro MatsuokaShigeki Matsunaga
Oct 22, 2020·The Journal of Organic Chemistry·Yujiro Hayashi

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Methods Mentioned

BETA
column chromatography

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