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Synlett 2017; 28(14): 1753-1757
DOI: 10.1055/s-0036-1589092
DOI: 10.1055/s-0036-1589092
cluster
A One-Pot Methodology for the Synthesis of the Yohimban Skeleton
Financial support for this research was provided by the Project CTQ2016-75350-P from the Ministry of Economy, Industry, and Competitiveness of Spain/FEDER funds. B.B. acknowledge the Serra Hunter programme (Generalitat de Catalunya)Weitere Informationen
Publikationsverlauf
Received: 01. Juni 2017
Accepted after revision: 11. Juli 2017
Publikationsdatum:
15. August 2017 (online)


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 synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589092.
- Supporting Information