Revisiting a classic approach to the Aspidosperma alkaloids: An intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine

Rajesh Iyengar, Klaas Schildknegt, Martha Morton, Jeffrey Aubé

Research output: Contribution to journalArticle

88 Scopus citations

Abstract

A total synthesis of (+)-aspidospermidine (1) is described. The key reactions used in the synthesis of this pentacyclic Aspidosperma alkaloid were a deracemizing imine alkylation/Robinson annulation sequence, a selective "redox ketalization", and an intramolecular Schmidt reaction. A Fischer indolization step carried out on a tricyclic ketone mirrored the sequence reported by Stork and Dolfini in their classic aspidospermine synthesis.

Original languageEnglish (US)
Pages (from-to)10645-10652
Number of pages8
JournalJournal of Organic Chemistry
Volume70
Issue number26
DOIs
StatePublished - Dec 23 2005

ASJC Scopus subject areas

  • Organic Chemistry

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