Synthesis and stereochemistry of glaucoposterol A and strophasterol D

Shuntaro Sato, Yuka Taguchi, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

Abstract

The proposed structure of glaucoposterol A, a strophastane-type steroid of mushroom origin, has been synthesized from an aldol obtained in our previous synthesis of strophasterol F, a diastereomer of the proposed structure of glaucoposterol A. Based on the fact that the NMR data of natural glaucoposterol A are distinctly different from those of the synthetic material, but matches those of strophasterol F, we put forward a proposal that glaucoposterol A and strophasterol F are actually the same compound. In addition, the hitherto unknown stereochemistry of strophasterol D has been elucidated through synthesis of its two diastereomeric structures.

Original languageEnglish
Article number131129
JournalTetrahedron
Volume76
Issue number17
DOIs
Publication statusPublished - 2020 Apr 24

Keywords

  • Cycloaddition
  • Stereochemical determination
  • Steroid
  • Strophasterol
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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