A Stereochemical Model of the Veratrum Alkaloids

Journal Article (Journal Article)

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.

Full Text

Duke Authors

Cited Authors

  • Brambilla, R; Friary, R; Ganguly, A; Puar, MS; Topliss, JG; Watkins, R; McPhail, AT

Published Date

  • January 1, 1982

Published In

Volume / Issue

  • 47 / 21

Start / End Page

  • 4137 - 4145

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo00142a026

Citation Source

  • Scopus