Spirotryprostatin B
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3D model (JSmol)
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| C21H21N3O3 | |
| Molar mass | 363.41 g/mol |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Spirotryprostatin B is an indolic alkaloid found in the Aspergillus fumigatus fungus that belongs to a class of naturally occurring 2,5-diketopiperazines. Spirotryprostatin B and several other indolic alkaloids (including Spirotryprostatin A, as well as other tryprostatins and cyclotryprostatins) have been found to have anti-mitotic properties, and as such they have become of great interest as anti-cancer drugs. Because of this, the total syntheses of these compounds is a major pursuit of organic chemists, and a number of different syntheses have been published in the chemical literature.
The first total synthesis was accomplished in 2000 by the Danishefsky group at Columbia University, with a number of other syntheses following shortly thereafter by Williams, Ganesan, Fuji, Carreira, Horne, Overman, and most recently Trost.
From a synthetic point of view, the most challenging structural features of the molecule are the C3 spirocyclic ring juncture and the adjacent prenyl-substituted carbon. Approaches toward preparing the skeleton of spirotryprostatin B have varied considerably.
Danishefsky spirotryprostatin B synthesis
In the Danishefsky synthesis, an amine derived from tryptophan was condensed with an aldehyde, triggering a Mannich-type reaction wherein the pendant oxindole acted as a nucleophile toward the intermediate iminium species.
Williams spirotryprostatin B synthesis
The synthesis by the Williams group utilized a 3-component coupling reaction. A secondary amine was combined with an aldehyde to form an intermediate azomethine ylide, which underwent a 1,3-dipolar cycloaddition with an unsaturated oxindole also present in the reaction mixture.
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