Enantioselective total synthesis of sacrolide A

Tomoyo Mohri, Yusuke Ogura, Ryo Towada, Shigefumi Kuwahara

    Research output: Contribution to journalArticlepeer-review

    6 Citations (Scopus)

    Abstract

    An enantioselective total synthesis of sacrolide A, an antimicrobial and cytotoxic fourteen-membered macrolactonic oxylipin isolated from an edible freshwater cyanobacterium, has been accomplished from a known carboxylic acid in 20% overall yield by a concise ten-step sequence. The key transformations include chiral oxazolidinone-based diastereoselective installation of two hydroxy-bearing stereocenters, the Horner–Wadsworth–Emmons olefination to construct the full carbon skeleton, and the Shiina macrolactonization to establish the fourteen-membered macrolide structure.

    Original languageEnglish
    Pages (from-to)4011-4013
    Number of pages3
    JournalTetrahedron Letters
    Volume58
    Issue number42
    DOIs
    Publication statusPublished - 2017

    Keywords

    • Antimicrobial
    • Macrolide
    • Oxylipin
    • Sacrolide
    • Total synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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