Synthesis and antiviral activity of 11-azapentacyclo [6.2. 1.0. 2, 70.4, 1005, 9] decane

SL Sacks, JR Scheffer, CZ Teh…

Index: Sacks, Stephen L.; Scheffer, John R.; Teh, Chong-Ze; Tse, Allan Journal of Medicinal Chemistry, 1985 , vol. 28, # 6 p. 819 - 821

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Citation Number: 4

Abstract

The synthesis proceeded from the readily available Diels-Alder adducts 2a3 and 2b. 4 In what appears to be a general sequence, monoreduction of these enediones with sodium borohydride afforded the corresponding a-hydroxycyclohexenones 3a and 3b, which photocyclized (benzene, uranium glass filter) in good yield to give the ketols 4a and 4b. These compounds were oximated (syn/anti mixtures), and the synthesis was completed by ...