Abstract

The four C s -symmetric cis[n.3.1] bicyclic ketones where n=3,5,7, and 9 were acetalized with (R,R)-2,4-pentanediol, and the resulting derivatives were cleaved with triisobutylaluminum (TRIBAL). The first three examples, all of which have their polymethylene chain rigidly fixed in a diaxial orientation, undergo ring opening with very high diastereoselectivity. In the fourth case (n=9), the chain is sufficiently long to be attached in a diequatorial manner

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