Synthesis of (±)-aphanorphine: a new approach to tricyclic 3-benzazepine scaffold using two radical C-C bond-forming reactions

Takehiko Yoshimitsu, Chie Atsumi, Emiko Iimori, Hiroto Nagaoka, Tetsuaki Tanaka

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

An expeditious approach to (±)-aphanorphine has been established using readily available starting materials. The present synthesis relies on the direct assembly between N-methylpyrrolidone (NMP) and 2-bromoanisaldehyde, which takes place through Et3B/air-mediated transformation of the α-nitrogen-substituted sp3C-H bond, and features a new design concept for the synthesis of the tricyclic 3-benzazepine skeleton.

Original languageEnglish
Pages (from-to)4473-4475
Number of pages3
JournalTetrahedron Letters
Volume49
Issue number29-30
DOIs
Publication statusPublished - Jul 21 2008
Externally publishedYes

Fingerprint

Benzazepines
Skeleton
Scaffolds
Nitrogen
Air
aphanorphine
N-methylpyrrolidone

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of (±)-aphanorphine : a new approach to tricyclic 3-benzazepine scaffold using two radical C-C bond-forming reactions. / Yoshimitsu, Takehiko; Atsumi, Chie; Iimori, Emiko; Nagaoka, Hiroto; Tanaka, Tetsuaki.

In: Tetrahedron Letters, Vol. 49, No. 29-30, 21.07.2008, p. 4473-4475.

Research output: Contribution to journalArticle

Yoshimitsu, Takehiko ; Atsumi, Chie ; Iimori, Emiko ; Nagaoka, Hiroto ; Tanaka, Tetsuaki. / Synthesis of (±)-aphanorphine : a new approach to tricyclic 3-benzazepine scaffold using two radical C-C bond-forming reactions. In: Tetrahedron Letters. 2008 ; Vol. 49, No. 29-30. pp. 4473-4475.
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