Journal of Medicinal Chemistry p. 2306 - 2310 (1989)
Update date:2022-08-24
Topics:
Peters, Richard H.
Crowe, David F.
Avery, Mitchell A.
Chong, Wesley K. M.
Tanabe, Masato
Various estrane derivatives 1 reacted with cerium ammonium nitrate (CAN) selectively and efficiently to provide 9α,11β-difunctionalized derivatives 2, which were subsequently deoxygenated at C-9 with triethylsilane/boron trifluoride etherate to the desired target 11β-nitratoestranes 3a, 3b, and 5.When examined for estrogenic and postcoital antifertility activity, 11β-nitrates 2c, 2d, and 3b most notably displayed more potent oral activity than did ethynylestradiol.
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