A rational synthesis of bullvalene barbaralone and derivatives; bullvalone

WE Doering, BM Ferrier, ET Fossel, JH Hartenstein…

Index: Doering,W. von E. et al. Tetrahedron, 1967 , vol. 23, p. 3943 - 3963

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Citation Number: 86

Abstract

A rational synthesis of bullvalene (I) proceeds in seven steps from cycloheptatriene-7- carboxylic acid by way of cycloheptatriene-7-carbonyl chloride, cycloheptatrien-7-yl diazomethyl ketone (B-1), barbaralone (VI), bullvalone (V), 9-hydroxytricyclo [3.3. 2.02, 8] deca-3, 6-diene and 9-acetoxytricyclo-[3.3. 2.02, 8] deca-3, 6-diene (F-4). Discussion is concerned mainly with (a) an attempt to synthesize bullvalone (V) from cycloheptatriene-7- ...