Total synthesis and structural confirmation of the antibacterial diterpene leubethanol

Jessica Lu, Michael Perkins, Hans Griesser

    Research output: Contribution to journalArticlepeer-review

    11 Citations (Scopus)

    Abstract

    We report the total synthesis of leubethanol (1), a serrulatane compound that has recently been reported as having considerable antibacterial activity against multidrug-resistant bacteria, such as Staphylococcus aureus, and is of interest for applications in the control of bacterial biofilms in human medicine. Our synthetic route begins with (-)-isopulegol (4) and key steps include substrate directed hydroboration to generate the C1′ stereocentre and formation of the aromatic ring via the α-oxoketene-S,S-acetal intermediate 3. Overall the conversion of (-)-isopulegol (4) to leubethanol was achieved in 13 steps and an overall yield of 7%. Comparison of our spectroscopic data with those reported for leubethanol (1), isolated from Leucophyllum frutescens, verified the structure of the natural product.

    Original languageEnglish
    Pages (from-to)6468-6473
    Number of pages6
    JournalTetrahedron
    Volume69
    Issue number31
    DOIs
    Publication statusPublished - 5 Aug 2013

    Keywords

    • Serrulatane Leubethanol Antimicrobial Antibacterial Natural product

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