Transformation of Molecule 22 to Molecule 101 in the Synthesis of Cortistatin A
Cortistatin A is a steroid that has shown indications of inhibiting angiogenesis, but without any apparent cytotoxicity towards cancer cells. Shi et al. (2011) explored the synthesis of cortistatin A and related molecules using prednisone, a commercially available steroid, as the starting material with various reagents and reaction conditions. The authors wished to address the low availability of this steroid in hopes of being able to further study the effects and activity of cortistatin A in vivo. This project explores the transformation of molecule 22 to molecule 101 through a two-step reaction. Molecule 101 is the last intermediate in the synthesis of cortistatin A, and differs only by the existence of a pi bond in the five-membered ring.
Shi, J.; Manolikakes, G.; Yeh, C.-H.; Guerrero, C. A.; Shenvi, R. A.; Shigehisa, H.; Baran, P. S. J. Am. Chem Soc. 2011, 133, 8014-8027.