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), 4685-4693. (doi: 10.1021/jo000306o).
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Description/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.
| Item Type: | Article |
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| Related URLs: | |
| Keywords: | mammalian-cell cycle, aspergillus-fumigatus, spirotryprostatin-a, oxindole alkaloids, tryprostatin-a, stereoselective synthesis, g2/mphase, inhibitors, derivatives, fumitremorgins |
| Subjects: | Q Science Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 19068 |
| Date Deposited: | 18 Jan 2006 |
| Last Modified: | 01 Jun 2011 01:47 |
| Contributors: | Wang, H. S. (Author) Ganesan, A. (Author) |
| Date: | 28 July 2000 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/19068 |
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