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Rearrangements of methyl 9β-hydroxy-11-oxo-(-)-kauran-19-oate to diterpene skeletons with new ring systems

Publication ,  Journal Article
Nakano, T; Aracelis Maillo, M; Usubillaga, A; McPhail, AT; McPhail, DR
Published in: Tetrahedron Letters
December 23, 1991

On treatment with boron trifluoride etherate-acetic anydride-acetic acid, the 9β-hydroxy-11-oxo derivative 1c of methyl(-)-kaur-9(11)-en-19-oate did not form a pinacolic type of rearrangement product (B-homo derivative), but instead it yielded compounds 2 and 3. With boron trifluoride etherate-acetic anhydride, however, compound 1c underwent a profound backbone rearrangement leading to the formation of compound 4a. © 1991.

Duke Scholars

Published In

Tetrahedron Letters

DOI

ISSN

0040-4039

Publication Date

December 23, 1991

Volume

32

Issue

52

Start / End Page

7667 / 7670

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 3101 Biochemistry and cell biology
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

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Nakano, T., Aracelis Maillo, M., Usubillaga, A., McPhail, A. T., & McPhail, D. R. (1991). Rearrangements of methyl 9β-hydroxy-11-oxo-(-)-kauran-19-oate to diterpene skeletons with new ring systems. Tetrahedron Letters, 32(52), 7667–7670. https://doi.org/10.1016/0040-4039(91)80560-S
Nakano, T., M. Aracelis Maillo, A. Usubillaga, A. T. McPhail, and D. R. McPhail. “Rearrangements of methyl 9β-hydroxy-11-oxo-(-)-kauran-19-oate to diterpene skeletons with new ring systems.” Tetrahedron Letters 32, no. 52 (December 23, 1991): 7667–70. https://doi.org/10.1016/0040-4039(91)80560-S.
Nakano T, Aracelis Maillo M, Usubillaga A, McPhail AT, McPhail DR. Rearrangements of methyl 9β-hydroxy-11-oxo-(-)-kauran-19-oate to diterpene skeletons with new ring systems. Tetrahedron Letters. 1991 Dec 23;32(52):7667–70.
Nakano, T., et al. “Rearrangements of methyl 9β-hydroxy-11-oxo-(-)-kauran-19-oate to diterpene skeletons with new ring systems.” Tetrahedron Letters, vol. 32, no. 52, Dec. 1991, pp. 7667–70. Scopus, doi:10.1016/0040-4039(91)80560-S.
Nakano T, Aracelis Maillo M, Usubillaga A, McPhail AT, McPhail DR. Rearrangements of methyl 9β-hydroxy-11-oxo-(-)-kauran-19-oate to diterpene skeletons with new ring systems. Tetrahedron Letters. 1991 Dec 23;32(52):7667–7670.
Journal cover image

Published In

Tetrahedron Letters

DOI

ISSN

0040-4039

Publication Date

December 23, 1991

Volume

32

Issue

52

Start / End Page

7667 / 7670

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 3101 Biochemistry and cell biology
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry