cis-Decahydroquinolines via Asymmetric Organocatalysis: Application to the Total Synthesis of Lycoposerramine Z

A concise synthesis of the Lycopodium alkaloid lycoposerramine Z is reported. Key to the strategy is a one-pot organocatalyzed Michael reaction followed by a domino Robinson annulation/intramolecular aza-Michael reaction promoted by LiOH, leading to enantiopure cis-decahydroquinolines.