Issue 7, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

The pyridinium reduction route to alkaloids: a synthesis of (±)-tashiromine

Roderick W. Bates*a  and  Jutatip Boonsombatb  

* Corresponding authors

a Chulabhorn Research Institute, Vibhavadi-Rangsit Highway, Laksi, Bangkok 10210, Thailand

b Department of Chemistry, Chulalongkorn University, Phaya Thai Road, Bangkok 10330, Thailand

Abstract

An indolizidine natural product, (±)-tashiromine, has been synthesized as a single diastereoisomer by a simple protocol. The key steps of the synthesis include a heterogeneous Sonogashira reaction and a stereoelectronically controlled reduction of a bicyclic pyridinium ion.

Graphical abstract: The pyridinium reduction route to alkaloids: a synthesis of (±)-tashiromine

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Article information

DOI
https://doi.org/10.1039/B100407G
Article type
Paper
Submitted
09 Jan 2001
Accepted
20 Feb 2001
First published
08 Mar 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 654-656

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The pyridinium reduction route to alkaloids: a synthesis of (±)-tashiromine

R. W. Bates and J. Boonsombat, J. Chem. Soc., Perkin Trans. 1, 2001, 654 DOI: 10.1039/B100407G

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