title: Synthesis of highly functionalized pyrrolidines as tunable templates for the direct access to (±)-coerulescine and the tricyclic core of martinellines.
abstract: An aza-Michael induced ring closure (aza-MIRC) tandem reaction of benzyl (2-bromoethyl)carbamate with various Michael acceptors is described. The N-Cbz-β-gem-disubstituted pyrrolidines thus obtained were proved to be versatile intermediates for the rapid access to both martinelline and spirooxindole backbones. An application of this strategy towards an expedient 4 step total synthesis of (±)-coerulescine is also presented.
authors: URCOM, EA 3221, INC3M, FR-CNRS 3038, UFR des Sciences & Techniques de l'Université du Havre, BP: 540, 25 rue Philippe Lebon, F-76058 Le Havre Cedex, France.
authors: Ronan
authors: R
authors: Le Goff
authors: Ata Martin
authors: AM
authors: Lawson
authors: Adam
authors: A
authors: Daïch
authors: Sébastien
authors: S
authors: Comesse
mesh_terms: D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000814:Aniline Compounds; D011758:Pyrroles; D011759:Pyrrolidines; D011804:Quinolines; C480174:coerulescine; C410408:martinelline