Divergent Total Syntheses of Isobatzellines A/B and Batzelline A

Yumi Yamashita, Louna Poignant, Juri Sakata, Hidetoshi Tokuyama

Research output: Contribution to journalArticlepeer-review

Abstract

Divergent total syntheses of isobatzellines A/B and batzelline A were accomplished. A fully substituted common indole intermediate bearing C-2 methylthio and C-5 chloro groups was constructed via ring expansion of benzocyclobutenone oxime sulfonate with NaSMe and a benzyne-mediated cyclization/functionalization sequence as the key steps. The total synthesis of isobatzelline B was achieved via formation of the iminoquinone structure by the redox-neutral acid-promoted C-5 proto-dechlorination of the common indole intermediate. The total syntheses of isobatzelline A and batzelline A were completed in a divergent manner by oxidation of the common indole intermediate using MnO2 or Mn(OAc)3, respectively.

Original languageEnglish
Pages (from-to)6239-6243
Number of pages5
JournalOrganic letters
Volume22
Issue number16
DOIs
Publication statusPublished - 2020 Aug 21

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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