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 journalArticle

2 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

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Chirality
Arabinose
Esters
Alcohols
Amino Acids
kaitocephalin

Keywords

  • Chirality transfer
  • Kaitocephalin
  • Sigmatropic rearrangement

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of kaitocephalin facilitated by three stereoselective allylic transposition reactions. / Sugai, Tomoya; Okuyama, Yuya; Shin, Jaehyun; Usui, Shunme; Hisada, Shoko; Osanai, Ryosuke; Oishi, Takeshi; Satou, Takaaki; Chida, Noritaka.

In: Chemistry Letters, Vol. 47, No. 4, 01.01.2018, p. 454-457.

Research output: Contribution to journalArticle

Sugai, Tomoya ; Okuyama, Yuya ; Shin, Jaehyun ; Usui, Shunme ; Hisada, Shoko ; Osanai, Ryosuke ; Oishi, Takeshi ; Satou, Takaaki ; Chida, Noritaka. / Synthesis of kaitocephalin facilitated by three stereoselective allylic transposition reactions. In: Chemistry Letters. 2018 ; Vol. 47, No. 4. pp. 454-457.
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AU - Hisada, Shoko

AU - Osanai, Ryosuke

AU - Oishi, Takeshi

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AU - Chida, Noritaka

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