Caballero, EsmeraldaAvendaño López, María CarmenMenéndez Ramos, José Carlos2026-03-022026-03-022003Caballero E, Avendaño C, Menéndez JC. Brief Total Synthesis of the Cell Cycle Inhibitor Tryprostatin B and Related Preparation of Its Alanine Analogue. J Org Chem 2003;68:6944–51. https://doi.org/10.1021/jo034703l.10.1021/jo034703l.https://hdl.handle.net/20.500.14352/133646Acknowledgment. We thank Dr. M. T. Ramos for helpful discussions. Financial support of this research from CICYT (Grant SAF-2000-0130) is also gratefully acknowledgedTryprostatin B was synthesized in 32% overall yield from the readily available dipeptide anhydride cyclo-(l-Trp-l-Pro). Its tandem C-3 prenylation/cyclization gave the corresponding pentacyclic pyrroloindole systems bearing a prenyl group at the indole C-3 position. These compounds were then submitted to acid-catalyzed opening of the newly formed ring, with concomitant migration of the prenyl group to the indole C-2 position. The alanine analogue of tryprostatin B was also prepared using a similar sequence. The successful implementation of this strategy strengthens the case for a biosynthetic route for the tryprostatins along similar lines.engjournal articlehttps://doi.org/10.1021/jo034703l.restricted accessAlcoholsMonomersPeptides and proteinsReactions productsQuímica orgánica (Química)2306 Química Orgánica