title: Cycloaddition reactions of imines with 3-thiosuccinic anhydrides: synthesis of the tricyclic core of martinellic acid.
abstract: Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce gamma-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion-pi repulsion in the transition state. The utility of this technique is demonstrated in a synthesis of the carbon framework common to the alkaloids martinellic acid and martinelline in five steps.
authors.affiliation: Broad Institute of Harvard and MIT, Chemical Biology Program, 7 Cambridge Center, Cambridge, MA 02142, USA.
authors.forename: Pui Yee
authors.initials: PY
authors.lastname: Ng
authors.forename: Craig E
authors.initials: CE
authors.lastname: Masse
authors.forename: Jared T
authors.initials: JT
authors.lastname: Shaw
mesh_terms: D000812:Anhydrides / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis*; D011804:Quinolines / Q000138:chemical synthesis*
chemical_list: D000812:Anhydrides; D007097:Imines; D011758:Pyrroles; D011804:Quinolines; C432345:martinellic acid