Total Syntheses of (+)-T988 B and (+)-T988 C through the AgNTf2-Mediated Coupling of Bromopyrroloindoline with Indole

Soichiro Sato, Azusa Hirayama, Hirofumi Ueda, Hidetoshi Tokuyama

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The total syntheses of (+)-T988 B and (+)-T988 C were accomplished in 19 and 18 steps, respectively, in 20.2 % overall yield. The indole segment was regioselectively introduced at the sterically hindered C10b position through a diastereoselective bromocyclization reaction and a subsequent AgNTf2-mediated Friedel–Crafts reaction. The dithiodioxopiperazine moiety was efficiently constructed through a one-pot radical-mediated C−H bromination/dehydrobromination procedure on the dioxopiperazine ring.

Original languageEnglish
Pages (from-to)54-58
Number of pages5
JournalAsian Journal of Organic Chemistry
Volume6
Issue number1
DOIs
Publication statusPublished - 2017 Jan 1

Keywords

  • alkaloids
  • bromocyclization
  • cross-coupling
  • oxidation
  • total synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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