Issue 4, 2011
From the journal:

Chemical Science

A synthesis of strychnine by a longest linear sequence of six steps†

David B. C. Martina  and  Christopher D. Vanderwal*a  

* Corresponding authors

a Department of Chemistry, University of California, 1102 Natural Sciences II Mail Code: 2025, Irvine, California, USA
E-mail: cdv@uci.edu

Abstract

Strychnine is synthesized via a longest linear sequence of six steps from commercially available starting materials. Key steps include a base-mediated intramolecular Diels–Alder reaction of a tryptamine-derived Zincke aldehyde, a Ru-catalyzed trans-hydrosilylation of 1,4-butynediol, and a tandem Brook rearrangement/intramolecular conjugate addition reaction that affords the Wieland–Gumlich aldehyde.

Graphical abstract: A synthesis of strychnine by a longest linear sequence of six steps

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Article information

DOI
https://doi.org/10.1039/C1SC00009H
Article type
Edge Article
Submitted
06 Jan 2011
Accepted
10 Jan 2011
First published
04 Feb 2011

Chem. Sci., 2011,2, 649-651

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A synthesis of strychnine by a longest linear sequence of six steps

D. B. C. Martin and C. D. Vanderwal, Chem. Sci., 2011, 2, 649 DOI: 10.1039/C1SC00009H

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