Total synthesis of (-)-agelastatin A: An SH2′ radical azidation strategy

Izuru Tsuchimochi, Yuta Kitamura, Hiroshi Aoyama, Shuji Akai, Keiyou Nakai, Takehiko Yoshimitsu

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A reagent generated from TMSN3/KMnO4/BnEt3NCl was found to promote an SH2′ radical azidation of a bromo silyl enol ether to furnish an azido silyl enol ether via olefin transposition. With the present azidation protocol, a new synthetic approach to agelastatin A, a potent antitumor marine alkaloid, has been established.

Original languageEnglish
Pages (from-to)9893-9896
Number of pages4
JournalChemical Communications
Volume54
Issue number71
DOIs
Publication statusPublished - Jan 1 2018

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Ether
Ethers
Alkaloids
Alkenes
Olefins
agelastatin A

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

Cite this

Total synthesis of (-)-agelastatin A : An SH2′ radical azidation strategy. / Tsuchimochi, Izuru; Kitamura, Yuta; Aoyama, Hiroshi; Akai, Shuji; Nakai, Keiyou; Yoshimitsu, Takehiko.

In: Chemical Communications, Vol. 54, No. 71, 01.01.2018, p. 9893-9896.

Research output: Contribution to journalArticle

Tsuchimochi, I, Kitamura, Y, Aoyama, H, Akai, S, Nakai, K & Yoshimitsu, T 2018, 'Total synthesis of (-)-agelastatin A: An SH2′ radical azidation strategy', Chemical Communications, vol. 54, no. 71, pp. 9893-9896. https://doi.org/10.1039/c8cc05697h
Tsuchimochi, Izuru ; Kitamura, Yuta ; Aoyama, Hiroshi ; Akai, Shuji ; Nakai, Keiyou ; Yoshimitsu, Takehiko. / Total synthesis of (-)-agelastatin A : An SH2′ radical azidation strategy. In: Chemical Communications. 2018 ; Vol. 54, No. 71. pp. 9893-9896.
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