Evolution of a Short Route to Strychnine by Using the Samarium Diiodide-Induced Cascade Cyclization as a Key Step

Beemelmanns C, Reissig H.-U. (2015) Evolution of a Short Route to Strychnine by Using the Samarium Diiodide-Induced Cascade Cyclization as a Key Step Chemistry - A European Journal 21(23), 8416-8425.

Abstract

This comprehensive report accounts the development of a highly diastereoselective samarium diiodide-induced cascade reaction of substituted indolyl ketones. The complexity-generating transformation with SmI2 allows the diastereoselective generation of three stereogenic centers including one quaternary center in one step. The obtained tetra- or pentacyclic dihydroindole derivatives are structural motifs of many monoterpene indole alkaloids, and their subsequent transformations gave way to one of the shortest approaches towards strychnine (14 % overall yield in ten steps, or 10 % overall yield in eight steps). During the course of this report we discuss the influence of substituents on the cyclization step, plausible mechanistic scenarios for the SmI2-induced cascade reaction, diastereoselective reductive amination, and regioselective dehydratization protocols towards the pentacyclic core structure of strychnos alkaloids.

Leibniz-HKI-Autor*innen

Christine Beemelmanns

Awards

Highlight in Chemistry Views: http://www.chemistryviews.org/details/ezine/7865381/A_Short_Route_to_Strychnine.html

Identifier

doi: 10.1002/chem.201500094

PMID: 25877308