Oxidation of methyl podocarpate and methyl 12-hydroxyabietan-8,11,13-trien-18-oate with thallium(III) perchlorate
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. © Royal Society of Chemistry.
Duke Scholars
Published In
DOI
ISSN
Publication Date
Start / End Page
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry
Citation
Published In
DOI
ISSN
Publication Date
Start / End Page
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry