title: Enantioselective total synthesis of (-)-minovincine in nine chemical steps: an approach to ketone activation in cascade catalysis.
abstract: Dressed to the nines: The first enantioselective total synthesis of (-)-minovincine has been accomplished in nine chemical steps and 13 % overall yield. A novel, one-step Diels-Alder/β-elimination/conjugate addition organocascade sequence allowed rapid access to the central tetracyclic core in an asymmetric manner. Boc=tert-butoxycarbonyl, LG=leaving group, PMB=para-methoxybenzyl.
authors.affiliation: Merck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ 08544-1009 (USA) http://www.princeton.edu/chemistry/macmillan/
authors.forename: Brian N
authors.initials: BN
authors.lastname: Laforteza
authors.forename: Mark
authors.initials: M
authors.lastname: Pickworth
authors.forename: David W C
authors.initials: DW
authors.lastname: Macmillan
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D007659:Ketones
keywords: alkaloids; enantioselectivity; natural products; organocatalysis; total synthesis