Concise total syntheses of ( –)-jorunnamycin A and (–)-jorumycin enabled by asymmetric catalysis

ScienceConcise total syntheses of ( –)-jorunnamycin A and (–)-jorumycin enabled by asymmetric catalysisBY ERIC R. WELIN, AURAPAT NGAMNITHIPORN, MAX KLATTE, GUILLAUME LAPOINTE, GERIT M. POTOTSCHNIG, MARTINA S. J. MCDERMOTT, DYLAN CONKLIN, CHRISTOPHER D. GILMORE, PAMELA M. TADROSS, CHRISTOPHER K. HALEY, KENJI NEGORO, EMIL GLIBSTRUP, CHRISTIAN U. GR ÜNANGER, KEVIN M. ALLAN, SCOTT C. VIRGIL, DENNIS J. SLAMON, BRIAN M. STOLTZSCIENCE18 JAN 2019 : 270-275 A route to two marine natural products distinct from the biosynthesis enables structural diversification for drug discovery.Jorumycin is a structurally complex, pentacyclic organic compound produced by a marine mollusk. The success of a similar compound, trabectedin, in treating certain types of cancer has focused attention on exploring jorumycin's pharmaceutical properties. Welin et al.developed a succinct route to synthesizing jorumycin and the closely related jorunnamycin A that deliberately diverges from the putative biosynthetic pathway underlying prior chemical syntheses. This route, which hinges on a carefully optimized asymmetric catalytic hydrogenation, can be easily modified to introduce unnatural structural diversity for functional optimization in further drug discovery research.
Source: Organometallic Current - Category: Chemistry Tags: Asymmetric Total synthesis Source Type: blogs