Concepedia

General Approach for the Synthesis of Sarpagine/Ajmaline Indole Alkaloids. Stereospecific Total Synthesis of the Sarpagine Alkaloid (+)-Vellosimine

Tao Wang, James M. Cook

Organic Letters · 2000 · 92 citations · 25 references

DOI

Concepts

Abstract

[reaction: see text] (+)-Vellosimine has been synthesized enantiospecifically in 27% overall yield from commercially available D-(+)-tryptophan methyl ester via the asymmetric Pictet-Spengler reaction and a stereocontrolled intramolecular palladium-coupling reaction as key steps.

References

25

Palladium-Catalyzed α-Arylation of Ketones

Michael Palucki, Stephen L. Buchwald · Journal of the American Chemical Society · 1997 · 594 citations

, , +8

Highly Active and Selective Catalysts for the Formation of α-Aryl Ketones

Joseph M. Fox, Xiaohua Huang, A. Chieffi et al. · Journal of the American Chemical Society · 2000 · 517 citations

, , +16

Simple, Highly Active Palladium Catalysts for Ketone and Malonate Arylation:  Dissecting the Importance of Chelation and Steric Hindrance

Motoi Kawatsura, John F. Hartwig · Journal of the American Chemical Society · 1999 · 459 citations

, , +16

General strategy for the stereocontrolled synthesis of Strychnos alkaloids: a concise synthesis of (.+-.)-dehydrotubifoline

Viresh H. Rawal, Christophe Michoud, Robert Monestel · Journal of the American Chemical Society · 1993 · 154 citations

, , +6

A General Synthetic Entry to <i>Strychnos</i> Alkaloids of the Curan Type via a Common 3a-(2-Nitrophenyl)hexahydroindol-4-one Intermediate. Total Syntheses of (±)- and (−)-Tubifolidine, (±)-Akuammicine, (±)-19,20-Dihydroakuammicine, (±)-Norfluorocurarine, (±)-Echitamidine, and (±)-20-Epilochneridine<sup>1</sup>

Josep Bonjoch, Daniel Solé, Silvina García-Rubio et al. · Journal of the American Chemical Society · 1997 · 121 citations

, , +11