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

Author:

Welin Eric R.1ORCID,Ngamnithiporn Aurapat1ORCID,Klatte Max1,Lapointe Guillaume1,Pototschnig Gerit M.1,McDermott Martina S. J.2,Conklin Dylan2ORCID,Gilmore Christopher D.1,Tadross Pamela M.1,Haley Christopher K.1,Negoro Kenji1ORCID,Glibstrup Emil1ORCID,Grünanger Christian U.1,Allan Kevin M.1ORCID,Virgil Scott C.1ORCID,Slamon Dennis J.2ORCID,Stoltz Brian M.1ORCID

Affiliation:

1. Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.

2. Division of Hematology/Oncology, Department of Medicine, Geffen School of Medicine at UCLA, Los Angeles, CA, USA.

Abstract

Journey to jorumycin 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. Science , this issue p. 270

Funder

National Science Foundation

American Cancer Society

National Institute of General Medical Sciences

Alexander von Humboldt-Stiftung

California HIV/AIDS Research Program

German Academic Exchange Service

Margaret E. Early Trust

Teva Pharmaceuticals Marc A. Goshko Memorial Grant Program

Royal Thai Government Scholarship program

Austrian Science Fund

Swiss National Science Foundation

Oticon Fonden

Knud Højgaards Fond

Publisher

American Association for the Advancement of Science (AAAS)

Subject

Multidisciplinary

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