title: Cross-coupling of cyclopropanols: concise syntheses of indolizidine 223AB and congeners.
abstract: A new synthetic method for indolizidine or pyrrolizidine alkaloids based on readily available and attractively functionalized cyclopropanols, as exemplified in concise syntheses of indolizidine (-)-223AB, its 3-epimer, (-)-indolizidine 239AB, and (-)-indolizidine 239CD, is reported. This work highlights the applications of SN2' alkylation and C-acylation of cyclopropanols to meet stereochemical challenges in natural product synthesis. Also included is diastereoselective cyclization of the resulting aminoallene adduct for bicyclic ring formation.
authors.affiliation: Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States.
authors.forename: Nagavaram Narsimha
authors.initials: NN
authors.lastname: Rao
authors.affiliation: Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States.
authors.forename: Bibhuti Bhusan
authors.initials: BB
authors.lastname: Parida
authors.affiliation: Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States.
authors.forename: Jin Kun
authors.initials: JK
authors.lastname: Cha
mesh_terms: D000215:Acylation; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D003500:Cyclization; D004988:Ethers, Cyclic / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D004988:Ethers, Cyclic; D007212:Indolizines; C413142:indolizidine 223AB; C410457:indolizidine 239CD; C043657:cyclopropanol