Regioselective hydrostannation of diarylalkynes directed by a labile ortho bromine atom: an easy access to stereodefined triarylolefins, hybrids of combretastatin A-4 and isocombretastatin A-4.
A series of triarylolefins bearing the combretastatin A-4 and the isocombretastatin A-4 cores were synthesized and evaluated. The cooperative ortho-effect of a labile bromine atom in the regioselective hydrostannation of unsymmetrical diarylalkynes leading to stereodefined triarylolefins is presented.
Rasolofonjatovo
Evelia
E
University Paris-Sud, CNRS, BioCIS-UMR 8076, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, 5 rue J.-B. Clément, Châtenay-Malabry, F-92296, France.
Provot
Olivier
O
Hamze
Abdallah
A
Bignon
Jérome
J
Thoret
Sylviane
S
Brion
Jean-Daniel
JD
Alami
Mouâd
M
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000480:Alkynes / Q000737:chemistry*; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D001966:Bromine / Q000737:chemistry*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002733:Chlorophenols / Q000737:chemistry*; D006801:Humans; D009947:Organotin Compounds / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000737:chemistry*; D013237:Stereoisomerism; D013267:Stilbenes / Q000737:chemistry*; D013379:Substrate Specificity
D000475:Alkenes; D000480:Alkynes; D000970:Antineoplastic Agents; D002733:Chlorophenols; D009947:Organotin Compounds; D010456:Peptides, Cyclic; D013267:Stilbenes; C510267:hydrostannane; C023490:complestatin; C058728:fosbretabulin; D001966:Bromine