Abstract
A short and highly enantiospecific (seven steps, 99% ee) synthesis of (+)-ochromycinone 2 in 19% overall yield is reported. Key steps are the regioselective Diels–Alder reaction of the juglone derivative 4 with the mixture of dienes 5 and 9 derived from 3-methylcyclohexanone (99% ee) and the photooxidation of 1-deoxyochromycinone 3 to the natural ketone 2 . A pronounced concentration dependence of the specific rotation was observed for (+)-ochromycinone 2 in CHCl 3.
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