title: Reagent-based, modular, tandem Michael approach for obtaining different indoline alkaloid-inspired polycyclic architectures.
abstract: A modular, reagent-based approach to obtain different indoline alkaloid-inspired, tetracyclic architectures is developed. With the use of TBSOTf as a Lewis acid, we report here a tandem Michael-based approach that led to the synthesis of a diastereomeric mixture of tetracyclic derivatives with two additional six-membered rings. By simply changing the Lewis acid to TMSOTf, we were able to obtain a different tetracyclic compound having additional functionalized 5- and 7-membered rings with complete stereocontrol.
authors.affiliation: Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, Canada K1A 0R6.
authors.forename: Jean-Louis
authors.initials: JL
authors.lastname: Brochu
authors.forename: Michael
authors.initials: M
authors.lastname: Prakesch
authors.forename: Gary D
authors.initials: GD
authors.lastname: Enright
authors.forename: Donald M
authors.initials: DM
authors.lastname: Leek
authors.forename: Prabhat
authors.initials: P
authors.lastname: Arya
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D007211:Indoles / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D007202:Indicators and Reagents; D007211:Indoles; D008698:Mesylates; D011083:Polycyclic Compounds; D014297:Trimethylsilyl Compounds; C053353:trimethylsilyl trifluoromethanesulfonate; C057812:indoline