title: Synthesis of Lepadiformine Using a Hydroamination Transform.
abstract: Dissection of lepadiformine by a double hydroamination transform affords a simple achiral amino diene. This reaction is accomplished in the forward sense by amine-directed hydroboration and an oxidative alkyl shift to nitrogen, both of which occur with high stereoselectivity to generate three stereogenic centers and the lepadiformine skeleton.
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: M Greg
authors.initials: MG
authors.lastname: Tabor
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Shenvi
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D000818:Animals; D003500:Cyclization; D015394:Molecular Structure; D013237:Stereoisomerism; D014561:Urochordata / Q000737:chemistry
chemical_list: D000470:Alkaloids; D000588:Amines; C431548:lepadiformine