Revisiting a classic approach to the Aspidosperma alkaloids

An intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine

Rajesh Iyengar, Klaas Schildknegt, Martha D Morton, Jeffrey Aubé

Research output: Contribution to journalArticle

82 Citations (Scopus)

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

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Alkaloids
Imines
Alkylation
Ketones
aspidospermidine

ASJC Scopus subject areas

  • Organic Chemistry

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Revisiting a classic approach to the Aspidosperma alkaloids : An intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine. / Iyengar, Rajesh; Schildknegt, Klaas; Morton, Martha D; Aubé, Jeffrey.

In: Journal of Organic Chemistry, Vol. 70, No. 26, 23.12.2005, p. 10645-10652.

Research output: Contribution to journalArticle

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