In an ongoing effort to study the environmental fate of endocrine-active steroid hormones, we report the formation of phenolic rearrangement products (3 and 4) with a novel 6,5,8,5-ring system following aqueous photolysis of dienogest (1) and methyldienolone(2). The structures were established by analysis of 2D NMR and HRMS data, and that of 3 was confirmed by X-ray diffraction analysis. These photoproducts exhibit progestogenic and androgenic activity, albeit with less potency than their parent compounds.
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Date of publication: 25 April 2019; American Chemical Society Publications: Organic Letters
Author information: Nicholas C. Pflug (1), Christopher J. Knutson (1); Dalma Martinovic-Weigelt (2); Dale C. Swenson (1); Kristine H. Wammer (3); David M. Cwiertney (4); & James B. Gloer (1)
(1) Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States
(2) Department of Biology, University of St. Thomas, St. Paul, Minnesota 55105, United States
(3) Department of Chemistry, University of St. Thomas, St. Paul, Minnesota 55105, United States
(4) Department of Civil & Environmental Engineering, University of Iowa, Iowa City, Iowa 52242, United States