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

    Keywords

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

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this