title: Stereocontrolled synthesis of the tricyclic ABC ring system of daphnicyclidin A.
abstract: An enantiocontrolled synthesis pathway has been developed to provide formation of tricyclic amine 7, representing the ABC ring system of the complex alkaloid daphnicyclidin A (1). Our efforts describe preparation of the Z-hexahydro-(1H)-azocine 29 and cyclization to construct the novel 4-azabicyclo[5.3.2]dodecane 31. Transannular reductive amination following the deprotection of 31 gave the desired tertiary amine 7.
authors.affiliation: Department of Chemistry, Indiana University , Bloomington, Indiana 47405, United States.
authors.forename: David R
authors.initials: DR
authors.lastname: Williams
authors.forename: Prolay K
authors.initials: PK
authors.lastname: Mondal
authors.forename: Seth A
authors.initials: SA
authors.lastname: Bawel
authors.forename: Partha P
authors.initials: PP
authors.lastname: Nag
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D031995:Saxifragaceae / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; C540244:daphnicyclidin A