A General Approach to the Quinolizidine Alkaloids via an Intramolecular Aza-[3 + 3] Annulation. Synthesis of (±)-2-Deoxy-Lasubine II.
The first success in constructing a member of quinolizidine family of alkaloids employing an intramolecular aza-[3 + 3] annulation strategy is described here. The key feature is the usage of vinylogous urethane tethered to a vinyl iminium intermediate with trifluoroacetate serving as the counter anion. The proof-of-concept is illustrated with the synthesis of 2-deoxy-lasubine II.
Zhang
Yu
Y
Division of Pharmaceutical Sciences and Department of Chemistry, 777 Highland Avenue, Rennebohm Hall University of Wisconsin, Madison, WI 53705.
Gerasyuto
Aleksey I
AI
Long
Quincy A
QA
Hsung
Richard P
RP