Beilstein J. Org. Chem.2023,19, 89–90, doi:10.3762/bjoc.19.8
” topics of the discipline under discussion.
Cross-coupling reactions are also of importance in organophosphorus chemistry. Taddei and co-workers applied an alternative method to the classical Hiraoreaction [1]. They utilized the Ni-catalyzed double Michaelis–Arbuzov reaction of bis(bromoaryl) species and
Beilstein J. Org. Chem.2018,14, 2838–2845, doi:10.3762/bjoc.14.262
, Hungary Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary 10.3762/bjoc.14.262 Abstract Novel 2- or 4-phosphonated 13α-estrone derivatives were synthesized via the Hiraoreaction. Bromo regioisomers (2- or 4-) of 13α-estrone and its 3-benzyl or 3-methyl ether were
; enzyme; 13α-estrone; Hiraoreaction; 17β-HSD1 inhibition; OATP2B1; STS; Introduction
The biosynthesis of estrogens occurs via various enzymatic routes. Cytochrome P450 aromatase catalyzes the conversion of nonaromatic steroids to estrogens [1]. Moreover, hydrolysis of estrone 3-sulfate, existing as a
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Here we disclose the synthesis of novel 2- or 4-substituted 13α-estrone derivatives 8–13 via the Hiraoreaction (Scheme 1). Diethyl phosphite (7a) or diphenylphosphine oxide (7b) were chosen as >P(O)H reagents and C–P couplings were planned under microwave irradiation using Pd-based catalysis
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Graphical Abstract
Scheme 1:
Pd-catalyzed C(sp2)–P couplings at C-2 or C-4 in the 13α-estrone series.