Concepedia

Total Synthesis of the Antipode of Alkaloid 205 B

Naoki Toyooka, Ayako Fukutome, Hiroyuki Shinoda, Hideo Nemoto

Angewandte Chemie International Edition · 2003 · 44 citations · 24 references

DOI

Concepts

Abstract

Forming the tetrasubstituted piperidine ring with stereocontrol in a Michael-type conjugate addition is a key step in the first enantioselective synthesis of the antipode 1 of alkaloid 205 B. The absolute stereochemistry of the natural product could be determined unambiguously by comparison of the optical rotations.

References

24

N-methoxy-n-methylamides as effective acylating agents

Steven Nahm, Steven M. Weinreb · Tetrahedron Letters · 1981 · 1.8K citations

, , +5

Pyridine-derived triflating reagents: An improved preparation of vinyl triflates from metallo enolates.

Daniel L. Comins, Ali Dehghani · Tetrahedron Letters · 1992 · 514 citations

, , +2

A Novel and Highly Stereoselective Intramolecular Formal [3+3] Cycloaddition Reaction of Vinylogous Amides Tethered withα,β-Unsaturated Aldehydes: A Formal Total Synthesis of (+)-Gephyrotoxin

Lin‐Li Wei, Richard P. Hsung, Heather M. Sklenicka et al. · Angewandte Chemie International Edition · 2001 · 118 citations

, , +11

A new method of olefin synthesis. Coupling of lithium dialkylcuprates with enol triflates

John E. McMurry, William J. Scott · Tetrahedron Letters · 1980 · 100 citations

, , +1

Intramolecular Mannich Reaction in the Asymmetric Synthesis of Polysubstituted Piperidines:  Concise Synthesis of the Dendrobate Alkaloid (+)-241D and Its C-4 Epimer

Franklin A. Davis, Bin Chao, Ashwin Rao · Organic Letters · 2001 · 99 citations

, , +7