Total synthesis of pteridic acids A and B

Takashi Nakahata, Shohei Fujimura, Shigefumi Kuwahara

    研究成果: Article査読

    15 被引用数 (Scopus)

    抄録

    Pteridic acid A (1) is a spirocyclic octaketide produced by the phytoepiphytic actinomycete Streptomyces hygroscopicus TP-A0451 and possesses potent plant-growth-promoting activity comparable to that of indole-3-acetic acid. The enantioselective total synthesis of this natural product was achieved by employing the Sn(OTf)2-mediated Evans aldol reaction and the Fukuyama acetylenic coupling reaction as the key C-C bond-forming steps producing 1 through a 14-step sequence in 22% overall yield from a known oxazolidinone derivative. MgBr2-mediated equilibration of an anomerically favored spirocyclic intermediate used for the synthesis of 1 brought about partial epimerization of the spirocenter to give the corresponding anomerically disfavored epimer, which was converted into pteridic acid B (11-epi-1), another plant-growth promoter of the same microbial origin.

    本文言語English
    ページ(範囲)4584-4593
    ページ数10
    ジャーナルChemistry - A European Journal
    12
    17
    DOI
    出版ステータスPublished - 2006 6月 2

    ASJC Scopus subject areas

    • 触媒
    • 化学 (全般)
    • 有機化学

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