title: One-pot synthesis of the tetracyclic framework of the aromatic erythrina alkaloids from simple furans.
abstract: Conversion of a simple furan into the intact erythrinane skeleton in one synthetic operation has been accomplished. The one-pot reaction sequence begins with singlet oxygen photooxygenation of the furan and proceeds via a 2-pyrrolidinone formation, cyclization of the pendant aldehyde moiety and an N-acyliminium ion formation and terminates with a Pictet-Spengler-type aromatic substitution. The method has been used to achieve a rapid and highly effective formal synthesis of erysotramidine.
authors.affiliation: Department of Chemistry, University of Crete, Vasilika Vouton, 71003 Iraklion, Crete, Greece.
authors.forename: Dimitris
authors.initials: D
authors.lastname: Kalaitzakis
authors.forename: Tamsyn
authors.initials: T
authors.lastname: Montagnon
authors.forename: Eirini
authors.initials: E
authors.lastname: Antonatou
authors.forename: Georgios
authors.initials: G
authors.lastname: Vassilikogiannakis
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D003500:Cyclization; D004895:Erythrina / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011760:Pyrrolidinones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D005663:Furans; D006576:Heterocyclic Compounds, 4 or More Rings; D011760:Pyrrolidinones; C492626:erysotramidine; C028537:2-pyrrolidone