The University of Southampton
University of Southampton Institutional Repository

A biomimetic total synthesis of (-)-spirotryprostatin B and related studies

Wang, H. S. and Ganesan, A. (2000) A biomimetic total synthesis of (-)-spirotryprostatin B and related studies Journal of Organic Chemistry, 65, (15), pp. 4685-4693. (doi:10.1021/jo000306o).

Record type: Article

Abstract

The prenylated natural products spirotryprostatin A and B derived from the Trp-Pro diketopiperazine also feature an oxidative rearrangement of the indole to form a spirooxindole. Synthetically, formation of the oxindole ring was stereoselectively accomplished by reaction of the appropriate indole precursor with N-bromosuccinimide. For optimum results, the oxidation should be carried out prior to diketopiperazine cyclization. In this manner, we have synthesized the tetrahydro- and dihydro- analogues of spirotryprostatin B in four steps from L-tryptophan methyl ester. The dihydro derivative was then converted to spirotryprostatin B by unsaturation of the pyrrolidine ring to a pyrroline, thus unambiguously confirming the structure of the natural product.

Full text not available from this repository.

More information

Published date: 28 July 2000
Keywords: mammalian-cell cycle, aspergillus-fumigatus, spirotryprostatin-a, oxindole alkaloids, tryprostatin-a, stereoselective synthesis, g2/mphase, inhibitors, derivatives, fumitremorgins

Identifiers

Local EPrints ID: 19068
URI: http://eprints.soton.ac.uk/id/eprint/19068
ISSN: 0022-3263
PURE UUID: 19d07b93-5765-43fc-819a-dc8d14ee81fc

Catalogue record

Date deposited: 18 Jan 2006
Last modified: 17 Jul 2017 16:33

Export record

Altmetrics

Contributors

Author: H. S. Wang
Author: A. Ganesan

University divisions

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×