Highly diastereoselective polycyclization of homo(polyprenyl) arene analogues bearing terminal siloxyvinyl groups was catalyzed by tin(IV) chloride (10 mol %). The cyclizations of tert-butyldiphenylsilyl and triisopropylsilyl polyenol ethers gave 4 alpha(equatorial)- and 4 beta(axial)-siloxypolycycles as major isomers, respectively. The strong nucleophilicity of pro-C(9), a (6E) geometry, and a bulky silyl group effectively favored the 4 alpha-preference, whereas the weak nucleophilicity of pro-C(9), a (6Z)-geometry, and less steric hindrance of a silyl group favored the 4 beta-preference.
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