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

研究成果: Article査読

13 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)5308-5311
ページ数4
ジャーナルOrganic letters
19
19
DOI
出版ステータスPublished - 2017 10月 6

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

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