Synthesis of (--)-lasubine(I) via a planar chiral [(eta6-arene)Cr(CO)3] complex.
Key steps of the synthesis of the Lythracaea alkaloid (--)-lasubine(I) are the formation of an enantiopure planar chiral arylaldehyde tricarbonylchromium complex and highly diastereoselective aza-Diels-Alder cycloaddition and intramolecular radical cyclization reactions to afford a quinolizidinone intermediate. Ketone reduction, desilylation, and decomplexation yield the enantiomerically pure product.
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Department of Organic Chemistry, University of Geneva, Switzerland.
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D000470:Alkaloids / Q000138:chemical synthesis*; D002384:Catalysis; D002857:Chromium; D009942:Organometallic Compounds; D019685:Rosales / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D009942:Organometallic Compounds; D002857:Chromium