The ester functionis then modified from a coenzyme A thioester to asimple methyl oxygen ester, and methylecgonine is subsequently obtained from the methoxycarbonyltropinoneby stereospecific reduction of the carbonyl. Note that,in this case, reduction of the carbonyl occurs from theopposite face to that noted with the tropinone → tropineconversion and, thus, yields the 3β configuration inecgonine. Cocaine is a diester of ecgonine, the benzoylmoiety arising from phenylalanine via cinnamic acid andbenzoyl-CoA (see page 157).
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