Abstract
The reaction of alcohol 13a with SOCl 2 gave 13b, 14a and 15a, and the reaction of chloride 13b with AgNO 3 (in MeO −/MeOH) gave 13c, 14b and 15b. In these reactions, 14a, 14b, 15a and 15b are the major products by sequential rearrangements. Treatment of the rearranged products 14a and 15a with KO t Bu (potassium tert-butoxide) gave 18 by an unusual isomerization. Compounds 19, 20 and 21 were also synthesized in different reactions. Compounds 14, 15, 19, 20 and 21 are all derivatives of anti-12-vinyltricyclo[6.3.1.0 2,7]dodeca-2,4,6,9-tetraene 19, and the syntheses of 19, 20 and 21 support the structures of compounds 14, 15 and 18.
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