Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 23
120
Views
11
CrossRef citations to date
0
Altmetric
Original Articles

Efficient Approach for the Synthesis of Novel Functionalized Isoxazolines from Limonene

, , , &
Pages 3617-3624 | Received 02 Feb 2006, Published online: 24 Nov 2006

References

  • Arai , M. A. , Shinohara , T. , Arai , T. and Sasai , H. 2004 . Development of the first spiro bis(isoxazoline) ligands (SPRIXs) and their applications to catalytic enantioselective reactions . Yuki gosei kagaku kyokaishi , 62 : 59 – 69 .
  • Quadrelli , P. , Scrocchi , R. , Caramella , P. , Rescifina , A. and Piperno , A. 2004 . From cyclopentadiene to isoxazoline‐carbocyclic nucleosides: a rapid access to biological molecules through nitrosocarbonyl chemistry . Tetrahedron , 60 : 3643 – 3651 .
  • Damkaci , F. and Deshong , P. 2003 . Stereoselective synthesis of α‐ and β‐glycosylamide derivatives from glycopyranosyl azides via isoxazoline intermediates . J. Am. Chem. Soc. , 125 : 4408 – 4409 .
  • Lemaire , M. , Veny , N. , Gefflaut , T. , Gallienne , E. , Chenevert , R. and Bolted , J. 2002 . First stereocontrolled reduction of isoxazoline by hydrogenolysis: A new route to iminosugars via cyclic sulfates . Synlett , : 1359 – 1361 .
  • Gefflaut , T. , Martin , C. , Delor , S. , Besse , P. , Veschambre , H. and Bolte , J. 2001 . Deoxysugars via microbial reduction of 5‐acyl‐isoxazolines: Application to the synthesis of 3‐deoxy‐d‐fructose and derivatives . J. Org. Chem. , 66 : 2296 – 2301 .
  • Jones , R. C. F. , Martin , J. N. , Smith , P. , Gelbrich , T. , Light , M. E. and Hursthouse , M. B. 2000 . Synthesis of ene‐1,1‐diamines and pyrrolo[1,2‐α]imidazolediones by 4,5‐dihydroimidazole‐n‐oxide cycloaddition and isoxazoline ring opening . Chem. Commun. , : 1949 – 1950 .
  • Merja , B. C. , Joshi , A. M. , Parikh , K. A. and Parikh , A. R. 2004 . Synthesis and biological evaluation of pyrido‐[1,2‐A]pyrimidine and isoxazoline derivatives . Indian J. Chem. Sect. B , 43 : 909 – 912 .
  • Lam , P. Y. S. , Adams , J. J. , Clark , C. G. , Calhoun , W. J. , Luettgen , J. M. , Knabb , R. M. and Wexler , R. R. 2003 . Discovery of 3‐amino‐4‐chlorophenyl P1 as a novel and potent benzamidine mimic via solid‐phase synthesis of an isoxazoline library . Bioorg. Med. Chem. Lett. , 13 : 1795 – 1799 .
  • Pirrung , M. C. , Tumey , L. N. , Raetz , C. R. H. , Jackman , J. E. , Snehalatha , K. , Mcclerren , A. L. , Fierke , C. A. , Gantt , S. L. and Rusche , K. M. 2002 . Inhibition of the antibacterial target UDP‐(3‐O‐acyl)‐N‐acetylglucosamine deacetylase (LpxC): Isoxazoline zinc amidase inhibitors bearing diverse metal binding groups . J. Med. Chem. , 45 : 4359 – 4370 .
  • Sielecki , T. M. , Liu , J. , Mousa , S. A. , Racanelli , A. L. , Hausner , E. A. , Wexler , R. R. and Olson , R. E. 2001 . Synthesis and pharmacology of modified amidine isoxazoline glycoprotein iib/iiia receptor antagonists . Bioorg. Med. Chem. Lett. , 11 : 2201 – 2204 .
  • Quan , M. L. , Ellis , C. D. , Liauw , A. Y. , Alexander , R. S. , Knabb , R. M. , Lam , G. , Wright , M. R. , Wong , P. C. and Wexler , R. R. 1999 . Design and synthesis of isoxazoline derivatives as factor Xa inhibitors, 21 . J. Med. Chem. , 42 : 2760 – 2773 .
  • Ziyat , H. , Ait Itto , M. Y. , Ait Ali , M. , Riahi , A. , Karim , A. and Daran , J.‐C. 2002 . Stereochemistry of two new polyfunctionalized gem‐dihalocyclopropanes . Acta Cryst. , C58 : 90 – 93 .
  • Fdil , N. , Ait Itto , M. Y. , Ait Ali , M. , Karim , A. and Daran , J.‐C. 2002 . Epoxydation Aérobique Des Terpènes Naturels: Etude De L'activité Catalytique Des Nouveaux Complexes Ru‐1,2,4‐Triazépines . Tetrahedron Lett. , 43 : 8769 – 8771 .
  • Feddouli , A. , El Kadib , A. , Rivière , P. , Delpech , F. , Rivière‐Baudet , M. , Castel , A. , Manriquez , M. J. , Chavez , I. , Ait Itto , M. Y. and Ahbala , M. 2004 . Photo‐induced single electron transfer addition of triphenylgermane to conjugated carbonyl compounds: Competitive radical addition . Appl. Organometal. Chem. , 18 : 233 – 240 .
  • Dakir , M. , Auhmani , A. , Ait Itto , M. Y. , Mazoir , N. , Akssira , M. , Pierrot , M. and Benharref , A. 2004 . Optimisation of allylic oxidation of (1s,3r,8r)‐2,2‐dichloro‐3,7,7,10‐tetramethyltricyclo[6,4,0,0 1,3]dodec‐9‐ene . Synth. Commun. , 34 : 2001 – 2008 .
  • Ziyat , H. , El Houssame , S. , Ait Ali , M. , Ait Itto , M. Y. , Karim , A. , Wartchow , R. and Butenschon , H. 2004 . Synthesis, structure, and absolute configuration of a new cyclopropanic compound derived from the sesquiterpene β‐himachalene . Z. Naturforsch. , 59B : 1177 – 1179 .
  • Feddouli , A. , Ait Itto , M. Y. , Hasnaoui , A. , Villemin , D. , Jaffres , P.‐A. , De O. Santos , J. S. , Riahi , A. , Huet , F. and Daran , J.‐C. 2004 . One pot diastereoselective synthesis of new chiral spiro‐1,3,4‐thiadiazoles and 1,4,2‐oxathiazoles from (1R)‐thiocamphor . J. Heterocycl. Chem. , 41 : 731 – 735 .
  • Ziyat , H. , Ait Ali , M. , Karim , A. , Meliet , C. , Castanet , Y. and Mortreux , A. 2004 . Catalytic oxidative cleavage of terpenic olefins: Useful route to chiral poly‐functionalised cyclobutanes and cyclopropanes . Acta Chim. Slov. , 51 : 223 – 230 .
  • Grundmann , C. and Dean , J. M. 1965 . Nitrile oxides V: Stable aromatic nitrile oxides . J. Org. Chem. , 30 : 2809 – 2812 .
  • Huisgen , R. and Mack , W. 1961 . 1.3 dipolare additionen der nitriloxyde an carbonylverbindungen . Tetrahedron Lett. , : 583 – 586 .
  • Huisgen , R. , Mack , W. and Anneser , E. 1961 . Die Synthese Von 1.2.4‐Oxdiazolen Aus Nitriloxyden Und Nitrilen . Tetrahedron Lett. , : 587 – 589 .
  • Tolédano , P. , Ait Itto , M. Y. and Hasnaoui , A. 1996 . 3‐Mésityl‐6‐méthyl‐7‐méthylthio‐4‐phényl‐6H‐isoxazolo[5,4‐e][1,2,4]triazépine . Acta Cryst. , C52 : 1230 – 1232 .
  • De Mattos , M. C. S. and Kover , W. B. 1994 . Ciclo‐Adição de Óxidos de Nitrila ao Limoneno: Síntese Químio e Regioespecífica de 2‐Isoxazolinas 3‐Substituídas . Quimica Nova , 17 : 119 – 123 .
  • Carlsen , J. , Katsuki , T. , Martin , V. S. and Sharpless , K. B. 1981 . A greatly improved procedure for ruthenium tetroxide catalyzed oxidations of organic compounds . J. Org. Chem. , 46 : 3936 – 3938 .
  • Rylander , P. N. 1973 . Organic Synthesis with Noble Metal Catalyst 133 New York : Academic Press .
  • Imajo , S. , Kuritani , H. , Shingu , K. and Nakagawa , M. 1979 . Absolute configuration of dimethyl tert‐butylsuccinate and tert‐butyl‐alpha‐naphthylacetic acid: Degradation of the aromatic ring with ruthenium tetroxide . J. Org. Chem. , 44 : 3587 – 3589 .
  • Tanji , S. , Kodaka , Y. , Shibata , T. and Soai , K. 2000 . Synthesis of chiral α‐acetoxy‐n‐acetylamides from chiral pyrimidylalkanols by the oxidative cleavage of pyrimidine ring . Heterocycles , 52 : 151 – 158 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.