Total synthesis of (–)-zephyranthine

Koki Ishii, Yuna Seki-Yoritate, Mizuki Ishibashi, Ming Wai Liaw, Takeshi Oishi, Takaaki Satou, Noritaka Chida

Research output: Contribution to journalArticle

Abstract

– Stereoselective total synthesis of (–)-zephyranthine 1 based on the chiral pool approach starting from D-arabinose is described. The three consecutive chiral centers in (–)-zephyranthine were effectively constructed by the sequential [3,3] sigmatropic rearrangements (Claisen, Overman, and Claisen rearrangements) with chirality transfer of the hydroxy groups in D-arabinose.

Original languageEnglish
Pages (from-to)111-117
Number of pages7
JournalHeterocycles
Volume99
Issue number1
DOIs
Publication statusPublished - 2019 Jan 1

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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  • Cite this

    Ishii, K., Seki-Yoritate, Y., Ishibashi, M., Liaw, M. W., Oishi, T., Satou, T., & Chida, N. (2019). Total synthesis of (–)-zephyranthine. Heterocycles, 99(1), 111-117. https://doi.org/10.3987/COM-18-S(F)40