Enantioselective Pd-Catalyzed Allylic Alkylation Reactions of Dihydropyrido[1,2-a]indolone Substrates: Efficient Syntheses of (−)-Goniomitine, (+)-Aspidospermidine, and (−)-Quebrachamine

Beau P. Pritchett, Jun Kikuchi, Yoshitaka Numajiri, Brian M. Stoltz

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

The successful application of dihydropyrido[1,2-a]indolone (DHPI) substrates in Pd-catalyzed asymmetric allylic alkylation chemistry facilitates rapid access to multiple alkaloid frameworks in an enantioselective fashion. Strategic bromination at the indole C3 position greatly improved the allylic alkylation chemistry and enabled a highly efficient Negishi cross-coupling downstream. The first catalytic enantioselective total synthesis of (−)-goniomitine, along with divergent formal syntheses of (+)-aspidospermidine and (−)-quebrachamine, are reported herein.

Original languageEnglish
Pages (from-to)13529-13532
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number43
DOIs
Publication statusPublished - 2016
Externally publishedYes

Keywords

  • alkaloids
  • allylic alkylation
  • asymmetric catalysis
  • quaternary centers
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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