Abstract
An enantioselective synthesis of cordiachromene is described. An allylic alcohol moiety is first attached in the o-position to the methoxymethoxy substituent in 1-methoxy-4-methoxymethoxybenzene. Then chirality is introduced successively through asymmetric Sharpless epoxidation on the allylic alcohol moiety and regioselective ring-opening. The chiral diol prepared is then cyclized to chromanmethanol with total retention of configuration. Chromenemethanol is obtained after bromination and dehydrobromination. The total synthesis is achieved by reaction between the tosylated chromene chiral moiety and an organomagnesium prenylated compound.
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