Total synthesis of spirotryprostatin A, leading to the discovery of some biologically promising analogues Journal Article
| Authors: | Edmondson, S.; Danishefsky, S. J.; Sepp-Lorenzino, L.; Rosen, N. |
| Article Title: | Total synthesis of spirotryprostatin A, leading to the discovery of some biologically promising analogues |
| Abstract: | The total synthesis of the title compound has been accomplished. A key step involves the oxidative rearrangement of the β-carboline derivative to an oxindole via the action of N-bromosuccinimide. From this point, a diketopiperazine was introduced. A thiophenyl group served as a precursor of the isopropylidene function. Implementation of the same sort of chemistry starting with a methoxytryptophan derivative led to the parent structures. Furthermore, it was shown that the difficultly accessible isopropylidene side chain of spirotryprostatin A is not necessary for biological activity. Moreover, three analogues lacking the diketopiperazine system were shown to be quite active as cell cycle inhibitors. |
| Keywords: | unclassified drug; antineoplastic agent; antineoplastic activity; drug structure; drug synthesis; structure analysis; oxidation; reaction analysis; article; spirotryprostatin a |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 121 |
| Issue: | 10 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 1999-03-17 |
| Start Page: | 2147 |
| End Page: | 2155 |
| Language: | English |
| DOI: | 10.1021/ja983788i |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 16 August 2016 -- Source: Scopus |
