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

A biomimetic total synthesis of (-)-spirotryprostatin B and related studies
A biomimetic total synthesis of (-)-spirotryprostatin B and related studies
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.
mammalian-cell cycle, aspergillus-fumigatus, spirotryprostatin-a, oxindole alkaloids, tryprostatin-a, stereoselective synthesis, g2/mphase, inhibitors, derivatives, fumitremorgins
0022-3263
4685-4693
Wang, H. S.
95a22b69-5405-4653-91d3-9bf3888c0b94
Ganesan, A.
62aa5a87-9308-4383-8686-99726b6bcfb9
Wang, H. S.
95a22b69-5405-4653-91d3-9bf3888c0b94
Ganesan, A.
62aa5a87-9308-4383-8686-99726b6bcfb9

Wang, H. S. and Ganesan, A. (2000) A biomimetic total synthesis of (-)-spirotryprostatin B and related studies. Journal of Organic Chemistry, 65 (15), 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.

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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

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Date deposited: 18 Jan 2006
Last modified: 15 Jul 2019 19:27

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Contributors

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

University divisions

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