title: A versatile enantioselective synthesis of azabicyclic ring systems: a concise total synthesis of (+)-grandisine D and unnatural analogues.
abstract: Closing in on azacines: We have developed a new six step approach for the rapid and enantioselective synthesis of indolizidine, pyrrolo[1,2-a]azepine, and pyrrolo[1,2-a]azocine azabicyclic systems and their respective lactam congeners, which are found in a host of natural products as well as pharmaceutical preparations. This protocol enables a concise enantioselective total synthesis of (+)-grandisine D in 16.4 % overall yield from commercial materials (see scheme).
authors.affiliation: Department of Chemistry, Vanderbilt University, Nashville, TN 37232-6600, USA.
authors.forename: Olugbeminiyi O
authors.initials: OO
authors.lastname: Fadeyi
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Senter
authors.forename: Kristopher N
authors.initials: KN
authors.lastname: Hahn
authors.forename: Craig W
authors.initials: CW
authors.lastname: Lindsley
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D053961:Azabicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D047029:Lactams, Macrocyclic / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D053961:Azabicyclo Compounds; D001688:Biological Products; D007212:Indolizines; D047029:Lactams, Macrocyclic; C546802:grandisine D