Oxygen → Idramantone

Participants

Reaction Steps

A mixture of 100 mmol of 5-hydroxy-2-adamantanone, 200 mmol of benzhydrol, 10 mmol of N-hydroxyphthalimide, 0.1 mmol of cobalt(II) acetate, and 200 ml of benzonitrile was stirred at 75° C. in an oxygen atmosphere (1 atm) for 6 hours. A reaction mixture was concentrated and was then subjected to column chromatography on a silica gel to yield 1-hydroxy-4-oxatricyclo[4.3.1.13,8]undecan-5-one of the following formula in a yield of 48% with a conversion rate from 5-hydroxy-2-adamantanone of 67%.

Provenance & Evidence