Synthesis of vinca alkaloids and related compounds. Part XCIII. Skeletal rearrangement of cyclovinblastine derivatives: Formation of a novel bisindole system

Katalin Honty, Ádám Demeter, Csaba Szántay, Miklós Hollósi, Pál Kolonits, Csaba Szántay

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11 Citations (Scopus)

Abstract

Bisindole alkaloids of the vinblastine (VLB) type can be oxidized to give a Ψ-aspidosperma-aspidosperma type skeleton via 3'-7'-transannular cyclization. Acid catalysis triggers an aspidospermane→eburnane skeletal rearrangement of these cyclic derivatives, thus giving a novel bisindole system with a Ψ-eburnea-aspidosperma type skeleton. A previously unexplored aspect of this transformation is the observed retention or inversion at C(16') depending on the starting C(16') configuration. The present paper gives a detailed account of the synthetic aspect of this work together with preliminary NMR and CD results concerning the epimerization at C(16').

Original languageEnglish
Pages (from-to)169-194
Number of pages26
JournalHeterocycles
Volume50
Issue number1
Publication statusPublished - Jan 1 1999

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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