Copper-mediated synthesis of coumestans via C(sp2)-H functionalization: Protective group free route to coumestrol and 4′-O-methylcoumestrol

A simple and efficient two step synthesis of coumestans is described. The key reaction in the synthesis is the use of easily available Cu(OAc)2 for C[sbnd]H functionalization of 3-(2-hydroxyphenyl)coumarin to give coumestan ring system via formal oxidative cyclization. This approach provided a short protective group free route to naturally occurring coumestrol and 4′-O-methylcoumestrol. © 2017 Elsevier Ltd

Authors
Naik M.M.1 , Kamat V.P.1 , Tilve S.G. 1, 2
Journal
Tetrahedron
Number of issue
37
Language
English
Pages
5528-5536
Status
Published
Link
External link
DOI
10.1016/J.TET.2017.07.057
Volume
73
Year
2017
Organizations
  • 1 Department of Chemistry, Goa University, Taleigao-Plateau, Goa 403 206, India
  • 2 Organic Chemistry Department, RUDN University, 6 Miklukcho-Maklaya Str.Moscow 117198, Russian Federation
Keywords
4′-O-methylcoumestrol; Copper acetate; Coumestans; Coumestrol; C[sbnd]H functionalization
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