A Stereochemical Model of the Veratrum Alkaloids
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.
Brambilla, R; Friary, R; Ganguly, A; Puar, MS; Topliss, JG; Watkins, R; McPhail, AT
Volume / Issue
Start / End Page
Electronic International Standard Serial Number (EISSN)
International Standard Serial Number (ISSN)
Digital Object Identifier (DOI)