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

Abstract

The reorganization of the carbon skeleton in a spiro cage dione to an unusual cage system, C19H24O2, 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.

Keywords

• crystal structure
• propellane
• cage system
• ring rearrangement
• ring-closing metathesis