Phosphine-catalyzed synthesis of 3,3-spirocyclopenteneoxindoles from γ-substituted allenoates: systematic studies and targeted applications.
The phosphine-promoted [3 + 2] cyclizations between γ-substituted allenoates and arylideneoxindoles have been applied to the stereoselective synthesis of spiro(cyclopentene)oxindoles with trisubstituted cyclopentene units. It has been demonstrated that PPh(3) operates a very efficient control of the relative stereochemistry of the three stereogenic centers of the final spiranic products. Focused experiments have been carried out then so as to access carbocyclic analogues of an important series of anticancer agents inhibiting MDM2-p53 interactions.
Institut de Chimie des Substances Naturelles-CNRS, UPR 2301, Centre de Recherche de Gif-1, av de la Terrasse, 91198 Gif-sur-Yvette, France.
Catherine
C
Gomez
Maxime
M
Gicquel
Jean-Christophe
JC
Carry
Laurent
L
Schio
Pascal
P
Retailleau
Arnaud
A
Voituriez
Angela
A
Marinetti
D000466:Alkadienes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010720:Phosphines; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
D000466:Alkadienes; D003517:Cyclopentanes; D007211:Indoles; D010720:Phosphines; D013141:Spiro Compounds; C044646:phosphine