AgNTf2-mediated allylation with allylsilanes at C3a-position of hexahydropyrroloindoles: Application to total syntheses of amauromine alkaloids

Hiroyuki Hakamata, Soichiro Sato, Hirofumi Ueda, Hidetoshi Tokuyama

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

A protocol for the allylation at the C3a-position of hexahydropyrroloindole using allylsilanes is developed. AgNTf2 proved to be an efficient activator of halopyrroloindoline substrates. This method is applicable to the introduction of various allyl groups including the reverse prenyl group. The utility of this reaction is demonstrated by total synthesis of amauromine alkaloids. Stepwise bromocyclizations of the bis-indolylmethyl diketopiperazine derivative and subsequent double reverse prenylation furnished (+)-novoamauromine and (-)-epiamauromine.

Original languageEnglish
Pages (from-to)5308-5311
Number of pages4
JournalOrganic letters
Volume19
Issue number19
DOIs
Publication statusPublished - 2017 Oct 6

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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