Synthesis of a New C-15 Phosphorus Ylide Used for the Preparation of Some β-End-Group Retinoid Derivatives

REFERENCES

• (a) Wittig , G. ; Rieber , M. Über die Metallierbarkeit von quaternären Ammonium- und Phosphonium-Salzen . Justus Liebigs Annalen der Chemie 1949 , 562 , 177 – 186 ; ( b ) Wittig , G. ; Rieber , M. Darstellung und Eigenschaften des Pentaphenyl-phosphors . Justus Liebigs Annalen der Chemie 1949 , 562 , 187 – 192 .
   Google Scholar
• Wittig , G. ; Geissler , G. Reactions of pentaphenylphosphorus and several of its derivatives . Ann. 1953 , 580 , 44 – 57 .
   Google Scholar
• Wittig , G. ; Schöllkopf , U. Über Triphenyl-phosphin-methylene als olefinbildende Reagenzien . Chem. Ber. 1954 , 97 , 1318 – 1330 .
   Google Scholar
• Pommer , H. ; Nürrenbach , A. Industrial synthesis of terpenes compounds . Pure Appl. Chem. 1975 , 43 , 527 – 551 .
   Web of Science ®Google Scholar
• Pommer , H. The Wittig reaction in industrial practice . Angew. Chem. 1977 , 89 , 437 – 443 .
   Google Scholar
• Pommer , H. ; Thieme , P. C. Industrial applications of the Wittig reaction . Top. Curr. Chem. 1983 , 109 , 165 – 188 .
   Google Scholar
• (a) Valla , A. ; Valla , B. ; Cartier , D. ; Le Guillou , R. ; Labia , R. ; Potier , P. New aromatic annulation Reaction via a C14 enaminone synthon: Synthesis of “terpenoid-like chalcones.” Tetrahedron Lett. 2005, 46, 6671–6674; (b) Valla , A. ; Cartier , D. ; Le Guillou , R. ; Labia , R. ; Schrevel , J. ; Potier , P. New syntheses and potential antimalaria activities of new “retinoic-like chalcones” Eur. J. Med. Chem. 2006, 41, 142–146.
   Web of Science ®Google Scholar
• (a) Benary , E. Über die Einwirkung von Ammoniak und Aminen auf einige aliphatische und aromatische Oxymethylen-ketone . Ber. 1930 , 63B , 1573 – 1577 ; ( b ) Normant , H. La chimie des organomagnésiens après Grignard . Pure Appl. Chem. 1972 , 30 , 463 – 498 ; ( c ) Jutz , C. Über ungesättigte Aldehyde und Ketone, II: Eine neue Reaktion magnesium-(lithium)-organischer Verbindungen . Ber. 1958 , 91 , 1867 – 1881 .
   Google Scholar
• Greenhill , J. V. Enaminones . Chem. Soc. Rev. 1977 , 6 , 277 – 294 .
   Web of Science ®Google Scholar
• For a review, see Michael , J. P. ; De Koning , C. B. ; Gravestock , D. ; Hosken , G. D. ; Howard , A. S. ; Jungmann , C. M. ; Krause , R. W. M. ; Parsons , A. S. ; Pelly , S. C. ; Stanburry , T. V. Enaminones: versatile intermediates for natural product synthesis . Pure Appl. Chem. 1999 , 71 , 979 – 988 .
   Web of Science ®Google Scholar
• (a) El-Taweel , F. M. , Elnagdi , M. H. J. Studies with enaminones: Synthesis of new coumarin-3-yl azoles, coumarin-3-yl azines, coumarin-3-ylazoloazines, coumarin-3-yl pyrone, and coumarin-2-yl benzo[b]furans . Heter. Chem. 2001 , 38 , 981 – 984 ; (b) Blache , Y. ; Benezech , V. ; Chezal , J.-M. ; Boule , P. ; Viols , H. ; Chavignon , O. ; Teulade , J.-C. ; Chapat , J.-P. Reactivity of heterocyclic enaminones: Regioselective synthesis of polyfused indolones . Heterocycles 2000 , 53 , 905 – 916 ; (c) Dawood , K. M. ; Kandeel , Z. E. ; Farag , A. M. Heterocyclic synthesis via enaminones: Regioselective synthesis of some novel pyrazole, isoxazole, pyrimidine, pyrido (1,2-a)benzimidazole and pyrazoto(1,5-a)-pyrimidine derivatives . Heteroatom Chem. 1999 , 10 , 417 – 422 ; (d) Blache , Y. ; Hichour , M. ; Di Blasi , G. ; Chezal , J.-M. ; Viols , H. ; Chavignon , O. ; Teulade , J.-C. ; Chapat , J.-P. Reactivity of heterocyclic enaminones: Regioselective synthesis of some pyridobenzodiazepines and imadazopyridines . Heterocycles 1999 , 51 , 1003 – 1014 ; (e) Friary , R. J. ; Seidl , V. ; Schwerdt , J. H. ; Chan , T.-M. ; Cohen , M. P. ; Conklin , E. R. ; Duelfer , T. ; Hou , D. ; Nafissi , M. ; Runkle , R. L. ; Tahbaz , P. ; Tiberi , R. L. ; Mc Phail , A. T. Intermolecular transaminations of enaminones: a synthesis of fused, polycyclic, N-aryl pyridones . Tetrahedron 1993 , 49 , 7179 – 7192 ; (f) Yang , S. C. ; Wang , H. M. ; Kuo , C. S. ; Chen , L. C. Copper(I) iodide–promoted cyclization of enaminones: Synthesis of 1,2,3,4-tetrahydro-4-oxo-β-carbolines . Heterocycles 1991 , 32 , 2399 – 2405 ; (g) Chan , T. M. ; Friary , R. ; Jones , H. ; Schwerdt , J. H. ; Seidl , V. ; Watnick , A. S. ; Williams , S. M. J. Transaminations of enaminomes: A synthesis of tricyclic, N-aryl, 1,2,3-triazole-fused pyridones . Heterocycl. Chem. 1990 , 27 , 1135 – 1142 .
   Web of Science ®Google Scholar
• Meyerhof , O. ; Lohmann , K. Über die enzymatische gleichgewichtsreaktionen zwischen hexosediphosphorsaure und dioxyacetonphosphorsaure . Bio. Chem. Z. 1934 , 271 , 89 – 110 .
   Google Scholar
• Corey , E. J. ; Erickson , B. W. Condensation of an allylic phosphonium ylide . J. Org. Chem. 1974 , 39 , 821 – 825 .
   Web of Science ®Google Scholar