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Backbone rearrangements of methyl (-)-kaur-9(11)-en-19-oate and its epoxide: structures of two diterpenes of a new skeletal type

Publication ,  Journal Article
Nakano, T; Spinelli, AC; Martín, A; Usubillaga, A; McPhail, AT; Onan, KD
Published in: Tetrahedron Letters
January 1, 1982

cleavage of the epoxide (2) of methyl (-)-kaur-9(11)-en-19-oate (1b) with boron trifluoride-ether in benzene and in acetic anhydride yielded (3a) and (3b), respectively. On epoxidation with m-chloroperbenzoic acid in the presence of N-nitrosomethyl urea, (1b) suffered a backbone rearrangement to form (6). © 1982.

Duke Scholars

Published In

Tetrahedron Letters

DOI

ISSN

0040-4039

Publication Date

January 1, 1982

Volume

23

Issue

35

Start / End Page

3627 / 3630

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., Spinelli, A. C., Martín, A., Usubillaga, A., McPhail, A. T., & Onan, K. D. (1982). Backbone rearrangements of methyl (-)-kaur-9(11)-en-19-oate and its epoxide: structures of two diterpenes of a new skeletal type. Tetrahedron Letters, 23(35), 3627–3630. https://doi.org/10.1016/S0040-4039(00)87690-X
Nakano, T., A. C. Spinelli, A. Martín, A. Usubillaga, A. T. McPhail, and K. D. Onan. “Backbone rearrangements of methyl (-)-kaur-9(11)-en-19-oate and its epoxide: structures of two diterpenes of a new skeletal type.” Tetrahedron Letters 23, no. 35 (January 1, 1982): 3627–30. https://doi.org/10.1016/S0040-4039(00)87690-X.
Nakano T, Spinelli AC, Martín A, Usubillaga A, McPhail AT, Onan KD. Backbone rearrangements of methyl (-)-kaur-9(11)-en-19-oate and its epoxide: structures of two diterpenes of a new skeletal type. Tetrahedron Letters. 1982 Jan 1;23(35):3627–30.
Nakano, T., et al. “Backbone rearrangements of methyl (-)-kaur-9(11)-en-19-oate and its epoxide: structures of two diterpenes of a new skeletal type.” Tetrahedron Letters, vol. 23, no. 35, Jan. 1982, pp. 3627–30. Scopus, doi:10.1016/S0040-4039(00)87690-X.
Nakano T, Spinelli AC, Martín A, Usubillaga A, McPhail AT, Onan KD. Backbone rearrangements of methyl (-)-kaur-9(11)-en-19-oate and its epoxide: structures of two diterpenes of a new skeletal type. Tetrahedron Letters. 1982 Jan 1;23(35):3627–3630.
Journal cover image

Published In

Tetrahedron Letters

DOI

ISSN

0040-4039

Publication Date

January 1, 1982

Volume

23

Issue

35

Start / End Page

3627 / 3630

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