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Oxidation of o-Isopropylphenol with Lead Tetraacetate: Synthesis of the Unit of Celastroidin Terpenes by the Diels-Alder Condensation

Jankowski C., Savoie A., Lesage D., Boivin D., Leclair G., Diaz T. E., Reyes-Chilpa R., Jimenez-Estrada M., Barrios H.

Polish Journal of Chemistry

2005

Vol. 79 / nr 2

429-440

Lead tetraacetate oxidation of o-isopropyl phenol under various conditions led to the dienone acetate which, when dimerized, represents a central part of the celastroidin penta- and hexa-terpenes (natural products from the Mexican shrub Hippocratea Celastroides). Six oxidation products formed in this reaction (the iso-propyl dienolone acetate, two dimers, benzoquinone, and two phenol acetates) were identified with help of 2D and 3D NMR, GC and LC-MS. From this, we concluded that the dimer skeleton observed for the dienolone acetate in natural products corresponded to the product from the photochemical pathway, and that the synthetic dimer has the opposite geometry; this was verified by molecular modelling. The oxidation of the second compound, o-cresol, leads to a similar profile of products.

X-ray, 1H/13C 2D and 3D NMR Studies of the Structures of Davallene and Adipedatol, Two Triterpenes Isolated from American Adiantum capillus-veneris

Jankowski C., Aumelas A., Thuery P., Reyes-Chilpa R., Jimenez-Estrada M., Barrios H., Diaz E.

Polish Journal of Chemistry

2004

Vol. 78 / nr 3

389-408

Two triterpenic compounds, Davallene 1and Adipedatol 2 were isolated from the roots of Mexican Adiantum capillus-veneris L. (Adiantaceae). The structures of both compounds are discussed on the basis of new 2D and 3DNMRspectroscopic and single crystal X-ray diffraction data.