Stereoselective Synthesis of the C27-C48 Moiety of Aflastatin A by a Carbohydrate Strategy Using a Tin(II)-Mediated Aldol Reaction

Sawato Murakoshi, Seijiro Hosokawa

    Research output: Contribution to journalArticle

    3 Citations (Scopus)

    Abstract

    The C27-C48 segment of aflastatin A was synthesized by using d-mannoside and l-erythrulose derivatives as chiral building blocks. The aldol reaction of undecan-2-one with mannolactone and a subsequent reduction gave the C37 and C39 stereogenic centers with high selectivity. Another aldol reaction of a tin(II) enolate of a protected erythrulose (C27-C30 segment) with a C31-C48 aldehyde segment gave the C30,C31-syn adduct with the desired stereochemistry. Deprotection of the assembled product proceeded smoothly to give the C27-C48 segment of aflastatin A containing a contiguous polyol moiety.

    Original languageEnglish
    Article numberst-2015-u0570-l
    Pages (from-to)2437-2441
    Number of pages5
    JournalSynlett
    Volume26
    Issue number17
    DOIs
    Publication statusPublished - 2015 Oct 22

    Fingerprint

    Tin
    Carbohydrates
    Mannosides
    Stereochemistry
    Aldehydes
    Derivatives
    erythrulose
    aflastatin A
    3-hydroxybutanal
    polyol
    undecan-2-one
    C 39

    Keywords

    • aflastatin A
    • aldol reactions
    • carbohydrates
    • polyols
    • stereoselectivity

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Stereoselective Synthesis of the C27-C48 Moiety of Aflastatin A by a Carbohydrate Strategy Using a Tin(II)-Mediated Aldol Reaction. / Murakoshi, Sawato; Hosokawa, Seijiro.

    In: Synlett, Vol. 26, No. 17, st-2015-u0570-l, 22.10.2015, p. 2437-2441.

    Research output: Contribution to journalArticle

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