RT Journal Article
T1 Brief Total Synthesis of the Cell Cycle Inhibitor Tryprostatin B and Related Preparation of Its Alanine Analogue
A1 Caballero, Esmeralda
A1 Avendaño López, María Carmen
A1 Menéndez Ramos, José Carlos
AB Tryprostatin 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.
PB American Chemical Society
YR 2003
FD 2003
LK https://hdl.handle.net/20.500.14352/133646
UL https://hdl.handle.net/20.500.14352/133646
LA eng
NO Caballero 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.
NO Acknowledgment. We thank Dr. M. T. Ramos for helpful discussions. Financial support of this research from CICYT (Grant SAF-2000-0130) is also gratefully acknowledged
DS Docta Complutense
RD 22 mar 2026