Synthesis of polycyclic cyclopropanecarboxylic acids and their esters based on catalytic cyclopropanation of 6,6-dimethylfulvene
Reactions of 6,6-dimethylfulvene with methyl diazoacetate in the presence of Cu compounds is accompanied by methoxycarbonylmethylenation of the endocyclic double bonds to give the corresponding mono- and diadducts in total yields of up to 85% with marked predominance ofanti-isomers. The subsequent cyclopropanation of monoadducts with diazomethane in the presence of Pd compounds also involves the endocyclic double bond and gives esters of tricyclo[18.104.22.168.2,4]heptanecarboxylic acid in high yields.
Key wordsdiazomethane diazoesters cyclopropanation esters of bicyclo[3.1.0]hex-2-ene-6-and tricyclo[4.1.0.02,4]heptane-3-carboxylic acids
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