An enantioselective organocatalytic approach to both enantiomers of lasubine II.
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.
Verkade
Jorge M M
JM
Radboud University Nijmegen, Institute for Molecules and Materials, Heyendaalseweg 135, NL-6525 AJ Nijmegen, The Netherlands.
van der Pijl
Ferdi
F
Willems
Marian M J H P
MM
Quaedflieg
Peter J L M
PJ
van Delft
Floris L
FL
Rutjes
Floris P J T
FP
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
D000470:Alkaloids; D011807:Quinolizines; C414385:lasubin I; D011392:Proline