A One-Pot Methodology for the Synthesis of the Yohimban Skeleton

Published as part of the ISHC Conference Special Section

Abstract

A simple and straightforward assembly of the yohimban skeleton was achieved by condensation of an acyclic β-keto ester with tryptamine, followed by consecutive cross metathesis and tandem cyclization reactions, leading to the formation of three new rings. The whole process was readily carried out in the one-flask providing a rapid entry to the pentacyclic scaffold of yohimbine alkaloids.

Key words

tandem cyclization - yohimbine alkaloids - intramolecular Michael reaction - organocatalysis - one-pot synthesis

• References and Notes

• 1 Current address: Research Center of the Man in the Desert – CIHDE, Av. General Velásquez 1775, Arica, Chile.

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