Polyhydroxylated indolizidine alkaloids - an efficient synthesis os 1-deoxy-8, 8a-epi-castanospermine

A.M.P. Koskinen, O.A. Kallatsa

    Research output: Contribution to journalArticleScientificpeer-review

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    Abstract

    A new and efficient enantioselective total synthesis of the title deoxycastanospermine derivative has been developed, based on amino acid and b-ketophosphonate chemistry, as well as employment of internal asymmetric induction for the creation of the new chiral centers proved successful. With proper choice of reaction conditions, the approach can also be applied in selective preparation of several isomers of deoxycastanospermine. The length (9 steps) and overall yield of the title compound trihydroxyindolidine 1, 7.3%, compares well with the literature syntheses of similar compounds.
    Original languageEnglish
    Pages (from-to)6947-6954
    JournalTetrahedron
    Volume59
    DOIs
    Publication statusPublished - 2003
    MoE publication typeA1 Journal article-refereed

    Keywords

    • asymmetric synthesis
    • natural products
    • organic chemistry

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