Tetrahedron p. 7289 - 7296 (1992)
Update date:2022-08-11
Topics:
Ghosh, Sukumar
Ghatak, Usha Ranjan
Whereas the (+/-)-podocarpa-8,11,13-trienes 3b-e, incorporating a phenolic hydroxyl or methyl ether functionality at C-11 and C-14, and C-14 respectively, on oxidation with sodium metaperiodate - catalyzed by ruthenium tetroxide give (+/-)-winterin, through chemoselective degradation of the aromatic ring, the unsubstituted 3a, isomeric methyl ethers 3f-i, and cis-podocarpa-8,11,13-triene undergo only benzylic oxidation resulting in the respective ketones 8d, 8a-c, 8e and the diketone 9.Similar oxidation reaction of the hexahydrophenanthrene 7a led to the α,β-unsaturated tricyclic ketone 11a and the tetrahydronaphthalene dicarboxylic anhydride 12.In contrast, 7b produced the diketone 10b and the α,β-unsaturated ketone 11b as the sole isolated products.
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