Synthesis of a cyclohexadiene monoepoxide by intramolecular Darzens condensation. Efficient synthesis of an A ring anthracyclinone precursor

…, RC Hawley, H Rapoport

Index: Bauman; Hawley; Rapoport Journal of Organic Chemistry, 1984 , vol. 49, # 20 p. 3791 - 3796

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Citation Number: 11

Abstract

Dimethyl P-methylglutaconate (5) 9 was prepared in 85% yield as a mixture of cis and trans isomers by base-catalyzed methanolysis of methyl isodehydroacetate. Bromine addition to glutaconate 5 (Scheme I) afforded dibromo derivative 6 which could be dehydrobrominated