Total syntheses and stereochemical reassignments of mollenines A and B

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

研究成果: Article査読

4 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)2766-2769
ページ数4
ジャーナルBioorganic and Medicinal Chemistry Letters
28
16
DOI
出版ステータスPublished - 2018 9 1
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 分子医療
  • 分子生物学
  • 薬科学
  • 創薬
  • 臨床生化学
  • 有機化学

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