title: Stereoselective one-step construction of vicinal quaternary and tertiary stereocenters of the 5,10b-ethanophenanthridine skeleton: total synthesis of (+/-)-maritidine.
abstract: The challenging vicinal quaternary and tertiary stereocenters of the 5,10b-ethanophenanthridine skeleton are created in a single step utilizing intramolecular [3 + 2]-cycloaddition of nonstabilized azomethine ylide as the key step. The application of the chemistry is demonstrated by synthesizing (+/-)-maritidine.
authors.affiliation: Division of Organic Chemistry, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411 008, India. gp.pandey@ncl.res.in
authors.forename: Ganesh
authors.initials: G
authors.lastname: Pandey
authors.forename: Nishant R
authors.initials: NR
authors.lastname: Gupta
authors.forename: Tukaram M
authors.initials: TM
authors.lastname: Pimpalpalle
mesh_terms: D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C544041:5,10b-ethanophenanthridine; D006576:Heterocyclic Compounds, 4 or More Rings; D010617:Phenanthridines; C476903:maritidine