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The reorganization of the carbon skeleton in a spiro cage dione to an unusual cage system, C 19 H 24 O 2 , using acid-promoted rearrangement with the aid of zinc dust as a reducing agent in the reaction medium is reported. The resulting trishomocubane hydroxyketone derivative includes five-membered rings having an envelope conformation and one seven-membered ring with a twist-chair conformation.

7-Hydroxyhexacyclo[7.5.1.01,7.06,13.08,12.010,14]pentadecan-15-one-11-spirocyclopentane

7-Hydroxyhexacyclo[7.5.1.0^1,7.0^6,13.0^8,12.0^10,14]pentadecan-15-one-11-spirocyclopentane