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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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
Digital Object Identifier (DOI): doi:10.1021/jo000306o
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
ePrint ID: 19068
Accepted Date and Publication Date:
28 July 2000Published
Date Deposited: 18 Jan 2006
Last Modified: 31 Mar 2016 11:35
URI: http://eprints.soton.ac.uk/id/eprint/19068

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