Synthetic studies on paspaline: Lewis acid-mediated sequential construction of a-e ring skeleton

Kentaro Okano, Yu Yoshii, Hidetoshi Tokuyama

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

The common pentacyclic skeleton of indole diterpene alkaloids, paspaline and its derivatives was constructed by a sequential reaction. The appropriate choice of the protecting group on the indole nitrogen was critical for the formation of bis(methylthio)allylic alcohol, which then underwent sulfonium ion formation and intramolecular electrophilic C-C-bond formation at the indole 3-position.

Original languageEnglish
Pages (from-to)1325-1334
Number of pages10
JournalHeterocycles
Volume84
Issue number2
DOIs
Publication statusPublished - 2012 Feb 7

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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