Total synthesis of (-)-leuconicine A and B
Gopal Sirasani1, Rodrigo B Andrade
1Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA.
Organic Letters
|August 5, 2011
Abstract:
Concise asymmetric total syntheses of Strychnos alkaloids (-)-leuconicine A (14 steps, 9% overall yield) and B (13 steps, 10% overall yield) have been accomplished. Key steps include (1) our sequential one-pot spiro-cyclization/intramolecular aza-Baylis-Hillman method to prepare the ABCE framework; (2) a novel domino acylation/Knoevenagel cyclization to prepare the F-ring; and (3) a Heck cyclization to access the D-ring.


