111427-86-2Relevant articles and documents
Total synthesis of spirotryprostatin a, leading to the discovery of some biologically promising analogues
Edmondson, Scott,Danishefsky, Samuel J.,Sepp-Lorenzino, Laura,Rosen, Neal
, p. 2147 - 2155 (2007/10/03)
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.
