Abstract
Controlled silylation of friedelin 1 from cork smoker wash solids gave 3-trimethylsiloxy-friedel-2-ene 3 or 3-trimethylsiloxy-friedel-3-ene 4 in high yields. Oxidation of 3 with m-chloroperbenzoic acid produced cerin 5 from which the 2,3-secofriedelan-2-al-3-oic acid (6) was obtained quantitatively by oxidation. Pachysandiol A 7 was obtained by selective reduction of cerin 5. A new nor seco acid derivative 8 was obtained in quantitative yield by oxidation of 3-hydroxyfriedel-3-en-2-one (2) with potassium permanganate. All the compounds were screened for antifungal activity.
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Moiteiro, C., Justino, F., Feio, S., Tavares, R., Marcelo-Curto, M.J., Florêncio, M.H. (2002). High Yield Synthesis of Friedelane and Seco Friedelane Derivatives from Cork Smoker Wash Solids. In: Rauter, A.P., Palma, F.B., Justino, J., Araújo, M.E., dos Santos, S.P. (eds) Natural Products in the New Millennium: Prospects and Industrial Application. Proceedings of the Phytochemical Society of Europe, vol 47. Springer, Dordrecht. https://doi.org/10.1007/978-94-015-9876-7_42
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DOI: https://doi.org/10.1007/978-94-015-9876-7_42
Publisher Name: Springer, Dordrecht
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