title: An enantioselective organocatalytic approach to both enantiomers of lasubine II.
abstract: A concise stereoselective route providing access to both enantiomers of the bioactive quinolizidine alkaloid lasubine II has been developed. The enantioselectivity was introduced by taking advantage of a proline-catalyzed asymmetric Mannich reaction. Next, the bicyclic system was constructed via a diastereoselective Mannich cyclization and subsequent ring-closing metathesis as the key steps.
authors.affiliation: Radboud University Nijmegen, Institute for Molecules and Materials, Heyendaalseweg 135, NL-6525 AJ Nijmegen, The Netherlands.
authors.forename: Jorge M M
authors.initials: JM
authors.lastname: Verkade
authors.forename: Ferdi
authors.initials: F
authors.lastname: van der Pijl
authors.forename: Marian M J H P
authors.initials: MM
authors.lastname: Willems
authors.forename: Peter J L M
authors.initials: PJ
authors.lastname: Quaedflieg
authors.forename: Floris L
authors.initials: FL
authors.lastname: van Delft
authors.forename: Floris P J T
authors.initials: FP
authors.lastname: Rutjes
mesh_terms: D000470:Alkaloids / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D011807:Quinolizines; C414385:lasubin I; D011392:Proline