Pot and time economies in the total synthesis of Corey lactone

Nariyoshi Umekubo, Yurina Suga, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1205-1209
Number of pages5
JournalChemical Science
Volume11
Issue number5
DOIs
Publication statusPublished - 2020

ASJC Scopus subject areas

  • Chemistry(all)

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