An expedient total synthesis of ent-(-)-7-deoxy-trans-dihydronarciclasine

Gábor Szántó, László Hegedus, Lenke Mattyasovszky, András Simon, Ákos Simon, István Bitter, Gábor Tóth, László Toke, István Kádas

Research output: Article

31 Citations (Scopus)

Abstract

A short and efficient stereoselective total synthesis of (-)-7-deoxy-trans-dihydronarciclasine, an ent-form of a highly potent antineoplastic agent constituent of the Amaryllidaceae alkaloids, is described. Starting from the enantiopure form of a known arylcyclohexylamine type precursor 6, which was synthesized enantioselectively utilizing a highly enantioselective nitromethane addition, the three hydroxy groups on the C-ring with the required stereochemistry were introduced by a chemo- and stereoselective enone reduction (NaBH4/CaCl2 system) followed by a Mitsunobu reaction and subsequent osmylation. The ring closure of the B-ring was accomplished by the Banwell modification of the Bischler-Napieralski reaction.

Original languageEnglish
Pages (from-to)8412-8417
Number of pages6
JournalTetrahedron
Volume65
Issue number40
DOIs
Publication statusPublished - okt. 3 2009

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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