Total synthesis of (±)-lennoxamine and (±)-aphanorphine by intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins

James R. Fuchs, Raymond L. Funk

Research output: Contribution to journalArticle

92 Citations (Scopus)

Abstract

equation presented Intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins constitute the key steps in the total syntheses of lennoxamine and aphanorphine. The aldehyde moiety of one cyclization product was transformed to a double bond, which was then engaged in a radical cyclization to produce the complete ring system of lennoxamine. The aldehyde functionality of the other cyclization product was converted to the corresponding mesylate, which underwent intramolecular displacement by a lactam enolate to furnish the ring system of aphanorphine.

Original languageEnglish (US)
Pages (from-to)3923-3925
Number of pages3
JournalOrganic Letters
Volume3
Issue number24
DOIs
StatePublished - Nov 29 2001

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Cyclization
aldehydes
Substitution reactions
substitutes
Aldehydes
rings
synthesis
products
Lactams
Mesylates
Chemical bonds
aphanorphine
lennoxamine

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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Total synthesis of (±)-lennoxamine and (±)-aphanorphine by intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins. / Fuchs, James R.; Funk, Raymond L.

In: Organic Letters, Vol. 3, No. 24, 29.11.2001, p. 3923-3925.

Research output: Contribution to journalArticle

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AB - equation presented Intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins constitute the key steps in the total syntheses of lennoxamine and aphanorphine. The aldehyde moiety of one cyclization product was transformed to a double bond, which was then engaged in a radical cyclization to produce the complete ring system of lennoxamine. The aldehyde functionality of the other cyclization product was converted to the corresponding mesylate, which underwent intramolecular displacement by a lactam enolate to furnish the ring system of aphanorphine.

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