Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin

Junxiu Meng, Tao Jiang, Huma Aslam Bhatti, Bina S. Siddiqui, Sally Dixon*, Jeremy Dunbar Kilburn

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    25 Citations (Scopus)

    Abstract

    Structural revision of lawsonicin, a natural product of Lawsonia alba, is reported based upon comparison of its spectral data with that of the naturally occurring dihydrobenzo[b]furan neolignan (rac)-trans-dihydrodehydrodiconiferyl alcohol, which is found to be identical. A concise synthesis of dihydrodehydrodiconiferyl alcohol, via Rh(2)[S-DOSP](4)-catalysed intramolecular C-H insertion, is described.

    Original languageEnglish
    Pages (from-to)107-113
    Number of pages7
    JournalOrganic & Biomolecular Chemistry
    Volume8
    Issue number1
    DOIs
    Publication statusPublished - 2010

    Keywords

    • C-H INSERTION
    • DIHYDROBENZOFURAN LIGNANS
    • BIOLOGICAL EVALUATION
    • CONIFERYL ALCOHOL
    • NEOLIGNANS
    • CONSTITUENTS
    • OXIDATION
    • POLYMERIZATION
    • BIOSYNTHESIS
    • INTERMEDIATE

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