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

Gábor Szántó, L. Hegedûs, Lenke Mattyasovszky, A. Simon, Ákos Simon, I. Bitter, Gábor Tóth, L. Tőke, István Kádas

Research output: Contribution to journalArticle

30 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 - Oct 3 2009

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Amaryllidaceae Alkaloids
Stereochemistry
Antineoplastic Agents
7-deoxy-trans-dihydronarciclasine
nitromethane

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

An expedient total synthesis of ent-(-)-7-deoxy-trans-dihydronarciclasine. / Szántó, Gábor; Hegedûs, L.; Mattyasovszky, Lenke; Simon, A.; Simon, Ákos; Bitter, I.; Tóth, Gábor; Tőke, L.; Kádas, István.

In: Tetrahedron, Vol. 65, No. 40, 03.10.2009, p. 8412-8417.

Research output: Contribution to journalArticle

Szántó, Gábor ; Hegedûs, L. ; Mattyasovszky, Lenke ; Simon, A. ; Simon, Ákos ; Bitter, I. ; Tóth, Gábor ; Tőke, L. ; Kádas, István. / An expedient total synthesis of ent-(-)-7-deoxy-trans-dihydronarciclasine. In: Tetrahedron. 2009 ; Vol. 65, No. 40. pp. 8412-8417.
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AU - Simon, Ákos

AU - Bitter, I.

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