Total syntheses and stereochemical reassignments of mollenines A and B

Shinya Shiomi, Kohei Wada, Yuhei Umeda, Hikaru Kato, Sachiko Tsukamoto, Hayato Ishikawa

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Total syntheses of prenylated pyrrolidinoindoline alkaloids, (−)-mollenines A [(−)-1′] and B (2′), were accomplished via three- and four-step sequences including a bioinspired indole prenylation reaction followed by dioxomorpholine ring formation. Then, the stereochemistry of mollenines A and B was reassigned to 3S,6S,14S,16S by analysis of spectroscopic data and chemical syntheses with different approaches along with the comparison of calculated and experimental ECD spectra. In addition, a thermodynamically controlled epimerization reaction on the dioxomorpholine ring was observed in our synthesis.

Original languageEnglish
Pages (from-to)2766-2769
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume28
Issue number16
DOIs
Publication statusPublished - 2018 Sep 1
Externally publishedYes

Keywords

  • Bioinspired reaction
  • Dioxomorpholine
  • Mollenine A
  • Mollenine B
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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