During the last decades Amaryllidaceae alkaloids (e.g. Lycorine, Galanthamine) have attracted the interest of chemists as target structures because of their various physiological effects such as acetylcholinesterase inhibition, immune-stimulation, antitumor-, antiviral- and antimalarial activities. In particular the focus of the research is on a total synthesis of the very potent Crinamine. The challenging structure of the Crinamine displays four chiral centers including a quaternary carbon center and a pentacyclic bridged ring phenanthroline system. In this connection an “ex-chiral-pool”-strategy from L-serine to build-up the chiral precursor lactone was developed. The olefin geometry of the lactone is adjusted by an acyclic Horner reaction of the according serine derivative and a subsequent intramolecular Heck coupling ring closure. A diastereoselective, intramolecular Stetter reaction was employed to generate the rigid bridged structure using the asymmetric induction of the adjacent stereogenic center. The final ring formation and the introduction of the missing stereogenic centers is topic of current investigation.

Synthesis of optically active crinine-type alkaloid precursors

253rd National Meeting (2017)

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