Vinyl and alkynyl pyrimidines as Michael acceptors: An approach to a cylindrospermopsin substructure

JF Djung, DJ Hart, ERR Young

Index: Djung, Jane F.; Hart, David J.; Young, Erick R.R. Journal of Organic Chemistry, 2000 , vol. 65, # 18 p. 5668 - 5675

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Citation Number: 18

Abstract

Vinyl pyrimidine 9 and alkynyl pyrimidine 24 undergo base-mediated intramolecular conjugate addition reactions in which a carbamate and a urea, respectively, behave as nitrogen nucleophiles. The cyclic carbamate derived from 9 was converted to 11 via a metalation-oxidation reaction in which 2-phenylsulfonyl-3-phenyloxaziridine behaves as a hydroxylation reagent. The cyclic urea derived from 24 was converted to ...