Two approaches to 14,15-secoergostane intermediates for the synthesis of strophasterols

Yuki Fukuda, Shuntaro Sato, Yusuke Ogura, Shigefumi Kuwahara

    Research output: Contribution to journalArticlepeer-review

    2 Citations (Scopus)

    Abstract

    Two protected 14,15-secoergostane derivatives suitable as pivotal intermediates for the synthesis of strophasterols A and B, anti-MRSA and neuronal cell-protecting natural products bearing a recently discovered strophastane skeleton, have been synthesized by two different routes. The first approach employed an oxidative cleavage of an α-hydroxy ketone intermediate with the Jones reagent as the key step to reach the targeted secoergostane from ergosterol in ten steps. In the second approach, an unprecedented reaction cascade composed of four reactions enabled us to obtain the secoergostane more efficiently in six steps.

    Original languageEnglish
    Pages (from-to)986-992
    Number of pages7
    JournalBioscience, Biotechnology and Biochemistry
    Volume82
    Issue number6
    DOIs
    Publication statusPublished - 2018

    Keywords

    • Cascade reaction
    • Oxidative cleavage
    • Secosteroid
    • Strophasterol

    ASJC Scopus subject areas

    • Biotechnology
    • Analytical Chemistry
    • Biochemistry
    • Applied Microbiology and Biotechnology
    • Molecular Biology
    • Organic Chemistry

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