Abstract
The pentacyclic alkaloid 1 could be synthesized by an intramolecular [4+2] cycloaddition reaction of intermediate 11, which had been obtained from tryptamine derivative 4 and aldehyde 5. After full epimerization of 13 the cyclization reaction furnished a mixture of 14a and 14b. Separation of the stereoisomers 14a and 14b and subsequent reduction with LiA1H 4 resulted in (±)-iboxyphylline (14a -> 1) and its epimer, (±)-20-epiiboxyphylline (14b -> 15).
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