Preparation of tricyclic lactam model compounds of renieramycin and saframycin anticancer natural products from common intermediate

Keiyo Nakai, Masashi Yokoya, Naoki Saito

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Tricyclic lactam model compounds of the left half (ABC ring) of renieramycin and saframycin anticancer natural products were prepared from common intermediate 6a. Readily available alcohol 6a was converted into enamide 8, and this was followed by transformation into 6b through a hydrobromination reaction in a stereoselective manner. Some diastereomers at C-6 to C-11a of the tricyclic lactam model compounds having several functional groups at C-6 were prepared from 6a or 6b in good yields. We presented also an unexpected reductive acetylation of the p-quinone to produce the corresponding 3,4-dehydro derivative.

Original languageEnglish
Pages (from-to)853-869
Number of pages17
JournalChemical and Pharmaceutical Bulletin
Volume61
Issue number8
DOIs
Publication statusPublished - Aug 1 2013

Keywords

  • Hydrobromination
  • Preparation
  • Reductive acylation
  • Renieramycin
  • Saframycin
  • Tetrahydroisoquinoline

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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