Enantioselective Total Synthesis of Cotylenin A

Masahiro Uwamori, Ryunosuke Osada, Ryoji Sugiyama, Kotaro Nagatani, Masahisa Nakada

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A convergent enantioselective total synthesis of cotylenin A is described. The A-ring fragment, prepared via the catalytic asymmetric intramolecular cyclopropanation developed in our laboratory, and the C-ring fragment, prepared from a known chiral compound via a modified acyl radical cyclization, were successfully assembled by the Utimoto coupling reaction. The formidable carbocyclic eight-membered ring of cotylenin A was efficiently constructed by a palladium-mediated cyclization. All the hydroxy groups in the scaffold were stereoselectively introduced, and a modified reducing reagent, Me4NBH(O2CiPr)3, has been developed. The sugar moiety fragment was prepared via three consecutive carbon-oxygen bond-forming reactions, and the glycosylation was accomplished using Wan's protocol.

Original languageEnglish
Pages (from-to)5556-5561
Number of pages6
JournalJournal of the American Chemical Society
Volume142
Issue number12
DOIs
Publication statusPublished - 2020 Mar 25

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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