Condensation of dimethoxybenzoylacetic acid with enzyme-generated (2) gives 3,4-dimethoxy-ω-(2-piperidyl)acetophenone (4), which by reaction with p-methoxyphenylacetaldehyde, and titanium(IV) chloride-catalysed cyclisation of the resultant enamine (6) leads to julandine (8); thallium(III) trifluoroacetate oxidation of (8) gives cryptopleurine (10).
R. B. Herbert, J. Chem. Soc., Chem. Commun., 1978, 794 DOI: 10.1039/C39780000794
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