Studies in biomimetic alkaloid syntheses. 8. Total syntheses of the C-14 epimeric hydroxyvincadifformines, tabersonine, a (hydroxymethyl)-D-norvincadifformine and …

…, FJ Okuniewicz, CL Kirkemo, JC Bohnert

Index: Kuehne, Martin E.; Okuniewicz, J. F.; Kirkemo, C. L.; Bohnert, J. C. Journal of Organic Chemistry, 1982 , vol. 47, # 7 p. 1335 - 1343

Full Text: HTML

Citation Number: 40

Abstract

Condensation of methyl 1, 2, 3, 4, 5, 6-hexahydroazepino [4, 5-b] indole-5-carboxyla~(6) with 5-chloro-2-ethyl-4-hydroxypentanal lactol (l4) yielded the 14a-and 14@- hydroxyvincadifformines (8a, b) in an epimeric ratio which was solvent dependent. On condensation of the indoloazepine 6 with 4, 5-epoxy-2-ethylpentanal (9) the same compounds were formed together with a (hydroxymethy1)-D-norvincadifformine, 10, as ...