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A Stereochemical Model of the Veratrum Alkaloids

Publication ,  Journal Article
Brambilla, R; Friary, R; Ganguly, A; Puar, MS; Topliss, JG; Watkins, R; McPhail, AT
Published in: Journal of Organic Chemistry
January 1, 1982
Published version (DOI)

A stereoselective synthesis beginning from the tetracyclic isoxazolidine 3 gave an inactive model (2) of rings D–F of the hypotensive Veratrum alkaloids (1). Cleaving, N-demethylating, and epimerizing 3 gave the amino alcohol 5a. Diazotizing 5a afforded lactamdiol 10, which retained the configuration of the carbinamine carbon of 5a. Reduction of the lactam of 10 yielded 2. Single-crystal X-ray analysis of 2 confirmed the assignment of relative stereochemistry at C6a and C11 of 2 and established that the solid-state conformation was all-chair. © 1982, American Chemical Society. All rights reserved.

Duke Scholars

Andrew T. McPhail
Author Andrew T. McPhail Chemistry

Published In

Journal of Organic Chemistry

DOI

10.1021/jo00142a026

EISSN

1520-6904

ISSN

0022-3263

Publication Date

January 1, 1982

Volume

47

Issue

21

Start / End Page

4137 / 4145

Related Subject Headings

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

Citation

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Brambilla, R., Friary, R., Ganguly, A., Puar, M. S., Topliss, J. G., Watkins, R., & McPhail, A. T. (1982). A Stereochemical Model of the Veratrum Alkaloids. Journal of Organic Chemistry, 47(21), 4137–4145. https://doi.org/10.1021/jo00142a026
Brambilla, R., R. Friary, A. Ganguly, M. S. Puar, J. G. Topliss, R. Watkins, and A. T. McPhail. “A Stereochemical Model of the Veratrum Alkaloids.” Journal of Organic Chemistry 47, no. 21 (January 1, 1982): 4137–45. https://doi.org/10.1021/jo00142a026.
Brambilla R, Friary R, Ganguly A, Puar MS, Topliss JG, Watkins R, et al. A Stereochemical Model of the Veratrum Alkaloids. Journal of Organic Chemistry. 1982 Jan 1;47(21):4137–45.
Brambilla, R., et al. “A Stereochemical Model of the Veratrum Alkaloids.” Journal of Organic Chemistry, vol. 47, no. 21, Jan. 1982, pp. 4137–45. Scopus, doi:10.1021/jo00142a026.
Brambilla R, Friary R, Ganguly A, Puar MS, Topliss JG, Watkins R, McPhail AT. A Stereochemical Model of the Veratrum Alkaloids. Journal of Organic Chemistry. 1982 Jan 1;47(21):4137–4145.
Journal cover image

Published In

Journal of Organic Chemistry

DOI

10.1021/jo00142a026

EISSN

1520-6904

ISSN

0022-3263

Publication Date

January 1, 1982

Volume

47

Issue

21

Start / End Page

4137 / 4145

Related Subject Headings

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