Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Enantioselective Total Synthesis of (+)-Wortmannin

Enantioselective Total Synthesis of (+)-Wortmannin
Tianfei Quan, Tuoping Luo, Yinliang Guo, Yandong Lu
A concise and enantioselective total synthesis of the potent PI3K inhibitor (+)-wortmannin is described. A Pd-catalyzed cascade reaction was first developed to connect a synthon derived from Hajos–Parrish ketone to a furan moiety. The subsequent Friedel–Crafts alkylation of the β-position of a furan ring to an epoxide was optimized to establish the C10 quaternary center. (+)-Wortmannin was eventually accomplished by transformations following a late-stage oxidation of the furan allylic position. Kinome profiling and in vitro enzymatic assays were performed on 17-β-hydroxy-wortmannin and an epoxide analogue.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b02515

DOI: 10.1021/jacs.7b02515

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