An efficient synthesis of antibiotic SF-2312 (3-dihydroxyphosphoryl-1,5- dihydroxy-2-pyrrolidone)

Tadashi Hanaya, Chika Itoh

    Research output: Contribution to journalArticlepeer-review

    7 Citations (Scopus)


    N-Benzyloxy-2-(diethoxyphosphoryl)pent-4-enamide (6) was prepared from ethyl diethoxyphosphorylacetate in a 3-step sequence. Oxidative cleavage of the terminal olefin of 6 with osmium tetroxide and sodium periodate afforded 1-benzyloxy-3-diethoxyphosphoryl-5-hydroxy-2-pyrrolidone (7). The first synthesis of racemic SF-2312 was achieved by treatment of 7 with trimethylsilyl bromide, followed by hydrogenolysis.

    Original languageEnglish
    Pages (from-to)1675-1683
    Number of pages9
    Issue number2
    Publication statusPublished - Feb 28 2010

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Pharmacology
    • Organic Chemistry


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