The chemistry of terpenes. Part XIII. Synthesis of (+)-3β, 7, 7-trimethyl-anti, cis, anti-tricyclo [4, 1, 0, 0 2, 4] heptane and (±)-trans-3-(1-hydroxyethyl)-6, 6-dimethylbicyclo …

PH Boyle, W Cocker, RL Gordon…

Index: Boyle,P.H. et al. Journal of the Chemical Society [Section] C: Organic, 1971 , p. 2127 - 2136

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Abstract

Syntheses of the novel, highly strained, tricyclic hydrocarbon,(+)-3β, 7, 7-trimethyl-anti, cis, anti-tricyclo [4, 1, 0, 02, 4] heptane (1) and of (±)-trans-3 (1-hydroxyethyl)-6, 6- dimethylbicyclo [3, 1, 0] hexane (2) are described. Cyclisation of the keto-aldehyde (10), obtained by the ozonolysis of (+)-car-3-ene (9) gives (+)-2-acetyl-6, 6-dimethylbicyclo [3, 1, 0] hex-2-ene (11), which with diazoethane affords the pyrazoline,(–)-1β-acetyl-3, 3, 7β- ...