A general strategy for the synthesis of indoloquinolizine alkaloids: Via a cyanide-catalyzed imino-Stetter reaction

Eunjoon Park, Cheol-Hong Cheon

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A new strategy applicable to the synthesis of indoloquinolizine natural products has been developed. A cyanide-catalyzed intramolecular imino-Stetter reaction of aldimines, derived from 2-aminocinnamic acid derivatives and 2-pyridinecarboxaldehydes, provided indole-3-acetic acid derivatives bearing a pyridyl ring at the 2-position. Reduction of the carboxylic acid moiety to an alcohol followed by activation of the resulting alcohol with Tf2O or TsCl generated indoloquinolizinium salts, which were utilized as precursors for indoloquinolizine natural products. The advantage of this protocol was successfully demonstrated in the total syntheses of arborescidine A and nauclefidine.

Original languageEnglish
Pages (from-to)10265-10275
Number of pages11
JournalOrganic and Biomolecular Chemistry
Volume15
Issue number48
DOIs
Publication statusPublished - 2017 Jan 1

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alkaloids
Cyanides
cyanides
Biological Products
Alkaloids
alcohols
Bearings (structural)
Alcohols
Derivatives
indoles
synthesis
products
Carboxylic Acids
acetic acid
carboxylic acids
Salts
Chemical activation
activation
salts
acids

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

A general strategy for the synthesis of indoloquinolizine alkaloids : Via a cyanide-catalyzed imino-Stetter reaction. / Park, Eunjoon; Cheon, Cheol-Hong.

In: Organic and Biomolecular Chemistry, Vol. 15, No. 48, 01.01.2017, p. 10265-10275.

Research output: Contribution to journalArticle

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