Synthesis of kaitocephalin facilitated by three stereoselective allylic transposition reactions

Tomoya Sugai, Yuya Okuyama, Jaehyun Shin, Shunme Usui, Shoko Hisada, Ryosuke Osanai, Takeshi Oishi, Takaaki Satou, Noritaka Chida

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

A stereoselective synthesis of kaitocephalin is described. The central strategy is based on chirality transfer reactions of three secondary alcohols derived from L-arabinose. The Overman rearrangement of an α,β-unsaturated ester, and intramolecular anti-type SN2¤ reaction constructed a β-hydroxy-α,α-disubstituted amino acid moiety. The third chirality transfer reaction is the Ichikawa rearrangement. These stereoselective reactions successfully established the three contiguous stereocenters embedded in kaitocephalin.

Original languageEnglish
Pages (from-to)454-457
Number of pages4
JournalChemistry Letters
Volume47
Issue number4
DOIs
Publication statusPublished - 2018 Jan 1

Keywords

  • Chirality transfer
  • Kaitocephalin
  • Sigmatropic rearrangement

ASJC Scopus subject areas

  • Chemistry(all)

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