title: Total synthesis of (+)-madangamine D.
abstract: Madangamines are a group of bioactive marine sponge alkaloids, embodying an unprecedented diazapentacyclic skeletal type. The enantioselective total synthesis of madangamine D has been accomplished, and represents the first total synthesis of an alkaloid of the madangamine group. It involves the stereoselective construction of the diazatricyclic ABC core using a phenylglycinol-derived lactam as the starting enantiomeric scaffold and the subsequent assembly of the peripheral macrocyclic rings. The synthesis provides, for the first time, a pure sample of madangamine D and confirms the absolute configuration of this alkaloid family.
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, 08028-Barcelona (Spain) http://www.ub.edu/sintefarma/
authors.forename: Roberto
authors.initials: R
authors.lastname: Ballette
authors.forename: Maria
authors.initials: M
authors.lastname: Pérez
authors.forename: Stefano
authors.initials: S
authors.lastname: Proto
authors.forename: Mercedes
authors.initials: M
authors.lastname: Amat
authors.forename: Joan
authors.initials: J
authors.lastname: Bosch
mesh_terms: D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; C583216:madangamine D
keywords: alkaloids; asymmetric synthesis; macrocycles; nitrogen heterocycles; total synthesis