title: General strategy for the construction of enantiopure pyrrolidine-based alkaloids. Total synthesis of (-)-monomorine.
abstract: An enantiopure cis-2,5-disubstituted pyrrolidine building block was prepared from cocaine. The synthetic utility of this compound as a chiral building block was demonstrated by a short and efficient synthesis of the pyrrolidine-based alkaloid (-)-monomorine (six steps, 37% overall yield).
authors.affiliation: Department of Chemistry, University of New Orleans, New Orleans, Louisiana 70148, USA.
authors.forename: Suhong
authors.initials: S
authors.lastname: Zhang
authors.forename: Liang
authors.initials: L
authors.lastname: Xu
authors.forename: Lei
authors.initials: L
authors.lastname: Miao
authors.forename: Hong
authors.initials: H
authors.lastname: Shu
authors.forename: Mark L
authors.initials: ML
authors.lastname: Trudell
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D007212:Indolizines; D011759:Pyrrolidines; C110223:indolizidine-195B; C032519:pyrrolidine