Total synthesis of Antofine by using Intramolecular 1.3-dipolar cycloaddition of Azidealkene

  • Lee, Jae-Kwang (Natural Products Research Institute, Seoul National University) ;
  • Lee, Tae-Ho (Natural Products Research Institute, Seoul National University) ;
  • Song , So-Young (Natural Products Research Institute, Seoul National University)
  • Published : 2002.10.01

Abstract

Antofine belongs to the Phenathroindolizidine group of alkaloids. This natural products exhibit interesting biological properties such as antitumour activity. and anti-inflammentory. Wittig reaction of phenathrenealdehyde with the phosponium salt provided the phenathreneazidealkene in good yield. Intramolecular 1.3-dipolar cycloaddition of the resulting azidealkent in refluxing benzene proceeded the imine. It was reduced with cyanoborohydride of Noyori's Asymmetric Hydrogenation. (omitted)

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