Synthesis of leuconoxine, leuconodine B, and rhazinilam by transformation of melodinine E via 6-hydro-21-dehydroxyleuconolam

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Abstract

Synthesis of monoterpene indole alkaloids, leuconoxine, leuconodine B, and rhazinilam, by transformation of melodinine E via 6-hydro-21-dehydroxyleuconolam was established. The pivotal intermediate, 6-hydro-21-dehydroxyleuconolam, was prepared from melodinine E via a ring-opening N,S-acetal formation of the diaza[5.5.6.6]fenestrane skeleton and subsequent chemoselective reduction. These results demonstrate that 6-hydro-21-dehydroxy-leuconolam is a useful synthetic precursor of these related monoterpene indole alkaloids.

Original languageEnglish
Article number131809
JournalTetrahedron
Volume79
DOIs
Publication statusPublished - 2021 Jan 22

Keywords

  • Aminal
  • Biomimetic synthesis
  • Divergent synthesis
  • Monoterpene indole alkaloid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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