Reagent-based, modular, tandem Michael approach for obtaining different indoline alkaloid-inspired polycyclic architectures.
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.
Brochu
Jean-Louis
JL
Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, Canada K1A 0R6.
Prakesch
Michael
M
Enright
Gary D
GD
Leek
Donald M
DM
Arya
Prabhat
P
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*
D000470:Alkaloids; D007202:Indicators and Reagents; D007211:Indoles; D008698:Mesylates; D011083:Polycyclic Compounds; D014297:Trimethylsilyl Compounds; C053353:trimethylsilyl trifluoromethanesulfonate; C057812:indoline