Issue 21, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

The total synthesis of (−)-suaveoline

Patrick D. Baileya  and  Keith M. Morgana  

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

Abstract

A new synthesis of the indole alkaloid (−)-suaveoline from L-tryptophan is reported (overall yield ca. 14%). Key synthetic steps include a high yielding cis-specific Pictet–Spengler reaction, a one-pot Horner–Wadsworth–Emmons and alkylation procedure, a vinylogous Thorpe cyclisation and the direct formation of a 3,4,5-trisubstituted pyridine from a 1,5-dinitrile. The direct conversion of ajmaline to semi-synthetic suaveoline is also described.

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/B005695M
Article type
Paper
Submitted
14 Jul 2000
Accepted
01 Sep 2000
First published
19 Oct 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 3578-3583

Permissions

Request permissions

The total synthesis of (−)-suaveoline

P. D. Bailey and K. M. Morgan, J. Chem. Soc., Perkin Trans. 1, 2000, 3578 DOI: 10.1039/B005695M

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements