title: Strategies toward the Total Synthesis of Calyciphylline B-type Alkaloids: A Computational Perspective Aided by DFT Analysis.
abstract: Herein we describe synthetic efforts toward the total synthesis of calyciphylline B-type alkaloids. In the process, we disclose a detailed DFT study of equilibrium geometries and transition states that explains the stereochemical outcome during the formation of critical intermediates. X-ray crystallographic analysis reveals interesting conformational features in the naturally occurring deoxycalyciphylline B and its synthetic congeners.
authors.affiliation: Department of Chemistry, Université de Montréal , Station Centre Ville, C.P. 6128, Montreal, Quebec H3C 3J7, Canada.
authors.forename: Amit Kumar
authors.initials: AK
authors.lastname: Chattopadhyay
authors.affiliation: Laboratoire de Chimie Pharmaceutique Organique, Campus Plaine CP205/5, Université Libre de Bruxelles , Boulevard du Triomphe, 1050 Brussels, Belgium.
authors.forename: Gilles
authors.initials: G
authors.lastname: Berger
authors.affiliation: Department of Chemistry, Université de Montréal , Station Centre Ville, C.P. 6128, Montreal, Quebec H3C 3J7, Canada.
authors.forename: Stephen
authors.initials: S
authors.lastname: Hanessian
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D019295:Computational Biology; D018360:Crystallography, X-Ray; D006576:Heterocyclic Compounds, 4 or More Rings; D007202:Indicators and Reagents; D008958:Models, Molecular; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; D007202:Indicators and Reagents; D011083:Polycyclic Compounds; C479142:calyciphylline B; C482084:deoxycalyciphylline B