Oxidation of methyl podocarpate and methyl 12-hydroxyabietan-8,11,13-trien-18-oate with thallium(III) perchlorate
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 1727-1731
- https://doi.org/10.1039/p19860001727
Abstract
On oxidation with thallium(III) perchlorate in aqueous perchloric acid, methyl podocarpate (5) yielded two products which were identified on the basis of spectral data as the p-quinol (8) and the aryl ketone (7a) which resulted from oxidation at C-7 remote from the aromatic ring c. When methyl 12-hydroxyabietan-8,11,13-trien-18-oate (6) was treated with the same reagent, a similar benzylic oxidation occurred yielding two aromatic compounds which spectroscopic analysis showed to be the aryl ketone (11) and the lactone (12) with a rearranged skeleton. The structure and stereochemistry of the latter product were established unequivocally by an X-ray crystallographic analysis. Possible mechanisms for the formation of compounds (7a), (11), and (12) are proposed.This publication has 2 references indexed in Scilit:
- Plant Anticancer Agents. XIII. Constituents of Austrocedrus chilensisJournal of Natural Products, 1983
- Tumor inhibitors having potential for interaction with mercapto enzymes and/or coenzymesBioorganic Chemistry, 1977