The oxidation of (+)-occidentalol with t-butyl chromate

Abstract

The oxidation of (+)-occidentalol (1) with t-butyl chromate affords 8-(1-hydroxy-1-methylethyl)-1,5-dimethyl-bicyclo[4,4,0]dec-4-ene-2,3-dione (3), (+)-2-hydroxy-9-(1-hydroxy-1-methylethyl)-2,6-dimethylbicyclo [4,4,0]-dec-4-en-3-one (4), (+)-3-[2-carboxy-5-(1-hydroxy-1-methylethyl)-2-methylcyclohexyl]but-2-enoic acid (6), and (+)-3-(1-hydroxy-1-methylethyl)-6,9-dimethyl-8-oxabicyclo[4,3,0]non-9-en-7-one (8). Mechanistic implications of the oxidation, based on the various products identified, are discussed.