5 years ago

De Novo Synthesis of Possible Candidates for the Inagami–Tamura Endogenous Digitalis-like Factor

De Novo Synthesis of Possible Candidates for the Inagami–Tamura Endogenous Digitalis-like Factor
Toshio Nishikawa, Keiko Hashimoto, Takahiro Shibata, Ai Ikeda, Atsuo Nakazaki
De novo synthesis of possible candidates for the Inagami–Tamura endogenous digitalis-like factor (EDLF) was achieved to validate a previously proposed structure. Our synthetic approach involves a highly regio- and diastereoselective Mizoroki–Heck reaction and a Friedel–Crafts-type cyclodehydration to construct steroidal tetracycle 14 as a versatile common intermediate leading to seven 2,14β-dihydroxyestradiol analogues 1ac, 2ac, and 3 as possible candidates. By comparing the potency of inhibitory activity against Na+/K+-ATPase between the synthesized candidates and the EDLF, it was found that the proposed structure is not likely to be a true structure of the Inagami–Tamura EDLF.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01640

DOI: 10.1021/acs.joc.7b01640

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