Synthesis of the Epimeric Secosteroids Strophasterols A and B

Shuntaro Sato, Yuki Fukuda, Yusuke Ogura, Eunsang Kwon, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Two epimeric rearranged ergostanes, strophasterols A and B, with an unprecedented carbon skeleton were synthesized from ergosterol, both in 17 steps via a common secosteroidal intermediate. The conversion of ergosterol into the pivotal intermediate involved an efficient acid-catalyzed double-bond migration from ring B to ring D, oxidative cleavage of the double bond, and a completely diastereoselective acyl radical cyclization to form an isolated cyclopentanone ring unique to this recently discovered family of steroidal compounds produced by mushrooms. The intermediate was transformed stereodivergently into two epimeric cyclopentane derivatives through hydrogenation using two types of catalysts. One epimer was elaborated into strophasterol B by utilizing peracid oxidation of an iodide to provide an epoxide directly, and the other epimer was elaborated into strophasterol A, which is known to be a suppressor of endoplasmic reticulum stress.

Original languageEnglish
Pages (from-to)10911-10914
Number of pages4
JournalAngewandte Chemie - International Edition
Volume56
Issue number36
DOIs
Publication statusPublished - 2017 Jan 1

Keywords

  • hydrogenation
  • radical reactions
  • steroids
  • strophasterol
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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