Pd-catalyzed reaction of sterically hindered hydrazones with aryl halides: synthesis of tetra-substituted olefins related to iso-combretastatin A4.
PdCl(2)(MeCN)(2) in combination with dppp proved to be a powerful and efficient catalyst for the coupling of sterically hindered N-arylsulfonylhydrazones with aryl halides, thus providing a flexible and convergent access to tetrasubstituted olefins related to iso-combretastatin A4 in good yields. This new protocol has been applied successfully to the formal synthesis of biphenylisopropylidene 4-pyridine CYP17 inhibitor, 12b, of biological interest.
Brachet
Etienne
E
University Paris-Sud 11, CNRS, BioCIS UMR 8076, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, 5 rue J.-B. Clément, Châtenay-Malabry F-92296, France.
Hamze
Abdallah
A
Peyrat
Jean-François
JF
Brion
Jean-Daniel
JD
Alami
Mouad
M
D000475:Alkenes / Q000138:chemical synthesis* / Q000494:pharmacology; D002384:Catalysis; D006219:Halogens / Q000737:chemistry*; D006835:Hydrazones / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013254:Steroid 17-alpha-Hydroxylase / Q000037:antagonists & inhibitors; D013267:Stilbenes / Q000737:chemistry* / Q000494:pharmacology; D014404:Tubulin / Q000737:chemistry
D000475:Alkenes; D006219:Halogens; D006835:Hydrazones; D013267:Stilbenes; D014404:Tubulin; D010165:Palladium; D013254:Steroid 17-alpha-Hydroxylase; C058728:fosbretabulin