Total Synthesis of Spirotryprostatin A, Leading to the Discovery of Some Biologically Promising Analogues
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- 作者：Scott Edmondson ; Samuel J. Danishefsky ; Laura Sepp-Lorenzino ; and Neal Rosen
- 刊名：Journal of the American Chemical Society
- 出版年：1999
- 出版时间：March 17, 1999
- 年：1999
- 卷：121
- 期：10
- 页码：2147 - 2155
- 全文大小：145K
- 年卷期：v.121,no.10(March 17, 1999)
- ISSN：1520-5126
文摘
The total synthesis of the title compound has been accomplished. A key step involves the oxidativerearrangement of the 
-carboline derivative to an oxindole via the action of N-bromosuccinimide. From thispoint, a diketopiperazine was introduced. A thiophenyl group served as a precursor of the isopropylidenefunction. Implementation of the same sort of chemistry starting with a methoxytryptophan derivative led tothe parent structures. Furthermore, it was shown that the difficultly accessible isopropylidene side chain ofspirotryprostatin A is not necessary for biological activity. Moreover, three analogues lacking the diketopiperazinesystem were shown to be quite active as cell cycle inhibitors.
-carboline derivative to an oxindole via the action of N-bromosuccinimide. From thispoint, a diketopiperazine was introduced. A thiophenyl group served as a precursor of the isopropylidenefunction. Implementation of the same sort of chemistry starting with a methoxytryptophan derivative led tothe parent structures. Furthermore, it was shown that the difficultly accessible isopropylidene side chain ofspirotryprostatin A is not necessary for biological activity. Moreover, three analogues lacking the diketopiperazinesystem were shown to be quite active as cell cycle inhibitors.