Synthesis of Tetracyclo[6.2.2.23,6.02,7]tetradeca-4,9,11,13-Tetraene |
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Authors: | Cheng-Tung Lin Bai-Ping Hwang Teh-Chang Chou |
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Abstract: | The title hydrocarbon 3, a C14H14 tetracyclic tetraene of C2v-symmetry, was synthesized by new routes starting from 1,8,9,10-tetrachloro-11,11-dimethoxytricyclo6.2.1.02,7]undeca-3,5,9-triene (1). The Diels-Alder cycloaddition of 1 with 2-chloroacrylyl chloride, a ketene equivalent, followed by subsequent reduction, dechlorination and deacctalization afforded the ketol 12 as a key intermediate. Elaboration of target compound 3 was carried out by either the method of ring enlargement of 12 or (better) the route of Diels-Alder reaction of decarbonylated 12 with trans-1,2-bis(phenylsulfonyl)ethcnc, an acetylene equivalent, to give trienol 17, followed by dehydration. Upon irradiation, 3 underwent intercyclic 2 + 2]-addition to caged hexacyclic diene 4. At 120°C, 3 decomposed into barrelene and benzene quantitatively. |
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Keywords: | Synthesis Tetracyclic tetraene [2+2]-photoaddition Diels-Alder reaction |
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