The absolute configuration of the fungal anthraquinone (+)-austrocorticin 1 is established as (R) by synthesis of its antipode 5 from (S)-(–)-but-3-yn-2-ol via a Diels–Alder reaction involving the highly functionalised, chiral butadiene 6. Similarly, austrocorticinic acid is made available from but-1-yne.
A. S. Cotterill, M. Gill, A. Giménez and N. M. Milanovic, J. Chem. Soc., Perkin Trans. 1, 1994, 3269 DOI: 10.1039/P19940003269
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