Preparation, Stereochemistry, and Nuclear Magnetic Resonance Spectroscopy of 4-Hydroxy(acetoxy)bicyclooctanes. Synthesis of (-)- and (+/-)-8,8-Dimethylbicyclooct-2-en-4-one

Article abstract of DOI:10.1021/jo00141a029

A potentially versatile intermediate for the synthesis of natural products containing the bicyclo<5.1.0>octane ring system is 8,8-dimethylbicyclo<5.1.0>oct-2-en-4-one (1).This intermediate was prepared efficiently in racemic form from 5-acetoxycycloheptene and in chiral form (1R,7S) from (-)-2-carene, via separate synthetic strategies.In addition, a number of 4-hydroxy(acetoxy)bicyclo<5.1.0>octanes (3, 4, and 6) were also prepared and their stereochemistry established rigorously by NMR spectroscopy and chemical correlation to 3t, the structure of which was determined by X-ray crystallographic analysis.