Issue 21, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

New asymmetric routes to ajmaline and suaveoline indole alkaloids

Patrick D. Bailey,a   Keith M. Morgan,a   David I. Smithb  and  John M. Vernonc  

a Chemistry Department, Heriot-Watt University, Edinburgh, Riccarton, UK

b Sanofi-Synthelabo Research, Alnwick, Northumberland, UK

c Chemistry Department, University of York, Heslington, York, UK

Abstract

The tetracyclic advanced intermediates 6, 8 and 9 obtained from L-tryptophan via a cis-selective Pictet–Spengler reaction and a Dieckmann–Thorpe cyclisation are used in a range of new approaches to polycyclic monoterpenoid indole alkaloids such as ajmaline and suaveoline. Structural modifications designed to facilitate a key intermolecular addition to C15 (ajmaline numbering) are described, followed by two intramolecular routes based on the addition of a suitable carbon fragment to a remote nitrogen atom prior to bond formation at C15.

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Article information

DOI
https://doi.org/10.1039/B005694O
Article type
Paper
Submitted
14 Jul 2000
Accepted
01 Sep 2000
First published
19 Oct 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 3566-3577

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New asymmetric routes to ajmaline and suaveoline indole alkaloids

P. D. Bailey, K. M. Morgan, D. I. Smith and J. M. Vernon, J. Chem. Soc., Perkin Trans. 1, 2000, 3566 DOI: 10.1039/B005694O

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