Function-Oriented Synthesis: Studies Aimed at the Synthesis and Mode of Action of 1α-Alkyldaphnane Analogues

An efficient synthetic route to the ABC tricyclic core of 1α-alkyldaphnanes has been developed. The conformational bias imparted by the C6−C9 oxo-bridge of BC-ring system 12 was used to elaborate the ABC-ring system precursor including the introduction of the β-C5 hydroxyl group. A completely diastereoselective palladium-catalyzed enyne cyclization was then employed to establish the A-ring with a C1 appendage.