Synlett 2017; 28(14): 1753-1757
DOI: 10.1055/s-0036-1589092
cluster
© Georg Thieme Verlag Stuttgart · New York

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

Claudio Parra
,
Pablo Solís
Laboratori de Química Orgànica, Facultat de Farmàcia, IBUB, Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain   Email: benbradshaw@ub.edu
,
Laboratori de Química Orgànica, Facultat de Farmàcia, IBUB, Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain   Email: benbradshaw@ub.edu
,
Laboratori de Química Orgànica, Facultat de Farmàcia, IBUB, Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain   Email: benbradshaw@ub.edu
› Author Affiliations
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)
Further Information

Publication History

Received: 01 June 2017

Accepted after revision: 11 July 2017

Publication Date:
15 August 2017 (eFirst)

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.

Supporting Information

 
  • References and Notes

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