Remote Asymmetric Bromination Reaction with Vinylketene Silyl N,O-Acetal and Its Application to Total Synthesis of Pellasoren A

Shinji Sekiya, Mao Okumura, Kei Kubota, Tatsuya Nakamura, Daisuke Sekine, Seijiro Hosokawa

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Stereoselective bromination of the E,E-vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved and applied to introduction of heteroatom at γ-position of α,β-unsaturated imide. The reactions proceeded in high stereoselectivity. Total synthesis of pellasoren A, an antitumor propionate from the myxobacteriun Sorangium cellulosum, has been accomplished in short steps by this methodology and our method of reduced polypropionate synthesis.

Original languageEnglish
Pages (from-to)2394-2397
Number of pages4
JournalOrganic Letters
Volume19
Issue number9
DOIs
Publication statusPublished - 2017 May 5

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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