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Oxidation of methyl podocarpate and methyl 12-hydroxyabietan-8,11,13-trien-18-oate with thallium(III) perchlorate

Publication ,  Journal Article
Nakano, T; Hernández, MI; Polachini, JM; Peña, DA; Corothie, E; Rojas, A; McPhail, AT
Published in: Journal of the Chemical Society, Perkin Transactions 1
January 1, 1986

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

Journal of the Chemical Society, Perkin Transactions 1

DOI

ISSN

1470-4358

Publication Date

January 1, 1986

Start / End Page

1727 / 1731

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

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Nakano, T., Hernández, M. I., Polachini, J. M., Peña, D. A., Corothie, E., Rojas, A., & McPhail, A. T. (1986). Oxidation of methyl podocarpate and methyl 12-hydroxyabietan-8,11,13-trien-18-oate with thallium(III) perchlorate. Journal of the Chemical Society, Perkin Transactions 1, 1727–1731. https://doi.org/10.1039/P19860001727
Nakano, T., M. I. Hernández, J. M. Polachini, D. A. Peña, E. Corothie, A. Rojas, and A. T. McPhail. “Oxidation of methyl podocarpate and methyl 12-hydroxyabietan-8,11,13-trien-18-oate with thallium(III) perchlorate.” Journal of the Chemical Society, Perkin Transactions 1, January 1, 1986, 1727–31. https://doi.org/10.1039/P19860001727.
Nakano T, Hernández MI, Polachini JM, Peña DA, Corothie E, Rojas A, et al. Oxidation of methyl podocarpate and methyl 12-hydroxyabietan-8,11,13-trien-18-oate with thallium(III) perchlorate. Journal of the Chemical Society, Perkin Transactions 1. 1986 Jan 1;1727–31.
Nakano, T., et al. “Oxidation of methyl podocarpate and methyl 12-hydroxyabietan-8,11,13-trien-18-oate with thallium(III) perchlorate.” Journal of the Chemical Society, Perkin Transactions 1, Jan. 1986, pp. 1727–31. Scopus, doi:10.1039/P19860001727.
Nakano T, Hernández MI, Polachini JM, Peña DA, Corothie E, Rojas A, McPhail AT. Oxidation of methyl podocarpate and methyl 12-hydroxyabietan-8,11,13-trien-18-oate with thallium(III) perchlorate. Journal of the Chemical Society, Perkin Transactions 1. 1986 Jan 1;1727–1731.

Published In

Journal of the Chemical Society, Perkin Transactions 1

DOI

ISSN

1470-4358

Publication Date

January 1, 1986

Start / End Page

1727 / 1731

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry