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

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Arabinose
Chirality
zephyranthine

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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

Total synthesis of (–)-zephyranthine. / Ishii, Koki; Seki-Yoritate, Yuna; Ishibashi, Mizuki; Liaw, Ming Wai; Oishi, Takeshi; Satou, Takaaki; Chida, Noritaka.

In: Heterocycles, Vol. 99, No. 1, 01.01.2019, p. 111-117.

Research output: Contribution to journalArticle

Ishii, K, Seki-Yoritate, Y, Ishibashi, M, Liaw, MW, Oishi, T, Satou, T & Chida, N 2019, 'Total synthesis of (–)-zephyranthine', Heterocycles, vol. 99, no. 1, pp. 111-117. https://doi.org/10.3987/COM-18-S(F)40
Ishii K, Seki-Yoritate Y, Ishibashi M, Liaw MW, Oishi T, Satou T et al. Total synthesis of (–)-zephyranthine. Heterocycles. 2019 Jan 1;99(1):111-117. https://doi.org/10.3987/COM-18-S(F)40
Ishii, Koki ; Seki-Yoritate, Yuna ; Ishibashi, Mizuki ; Liaw, Ming Wai ; Oishi, Takeshi ; Satou, Takaaki ; Chida, Noritaka. / Total synthesis of (–)-zephyranthine. In: Heterocycles. 2019 ; Vol. 99, No. 1. pp. 111-117.
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