Estrogen receptor ligands. 12. Synthesis of the major metabolites of an ERalpha-selective, dihydrobenzoxathiin antagonist for osteoporosis |
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Authors: | Kim Seongkon Wu Jane Y Zhang Zhoupeng Tang Wei Doss George A Dean Brian J Dininno Frank Hammond Milton L |
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Affiliation: | Department of Medicinal Chemistry, Merck Research Laboratories, P.O. Box 2000 (800B-109), Rahway, NJ 07065, USA. seongkon_kim@merck.com |
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Abstract: | [reaction: see text] During the course of drug metabolism studies, a major metabolite of compound 1 was detected in rhesus monkeys and assigned structure 4. The intriguing biotransformation of 1 leading to 4 was confirmed by a 19-step total synthesis starting from resorcinol (11), the key feature of which was the construction of the oxygen bridge utilizing a phenolic oxidation and trapping sequence. In addition, the synthesis of a related metabolite (5) is described. |
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