Solid-phase organic synthesis of 5-iodomethyl-dihydrofuran-2-ones with recyclable polymer-supported selenium bromide

Synthetic Communications

Volumn 42, Issue 3, 2012, Pages 320-327

  Wang, Chao Li ^a   Sheng, Shou Ri ^a   Cheng, Xin ^a   Cai, Ming Zhong ^a  

^a JIANGXI NORMAL UNIVERSITY   (China)

Author keywords

5 Iodomethyl dihydrofuran 2 one; Polystyrene supported selenium bromide; Recyclable; Selenium mediated intramolecular cyclization; Solid phase organic synthesis

Indexed keywords

3 BENZYL 5 IODOMETHYL DIHYDROFURAN 2 ONE; 3 ETHYL 5 IODOMETHYL DIHYDROFURAN 2 ONE; 3 METHYL 5 IODOMETHYL DIHYDROFURAN 2 ONE; 3,3 DIMETHYL 5 IODOMETHYL DIHYDROFURAN 2 ONE; 3,3 DIPHENYL 5 IODOMETHYL DIHYDROFURAN 2 ONE; 5 IODOMETHYL 5 METHYL DIHYDROFURAN 2 ONE; 5 IODOMETHYL 5 PHENYL DIHYDROFURAN 2 ONE; 5 IODOMETHYL DIHYDROFURAN 2 ONE; BROMIDE; FURAN DERIVATIVE; METHYL IODIDE; POLYMER; POLYSTYRENE; REAGENT; RESIN; SELENIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; SOLID PHASE SYNTHESIS;

EID: 80054694349     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.524064     Document Type: Article

References (47)

1. Nicolaou, K. C.; Hanko, R.; Hartwig, W.; Eds. Handbook of Combinatorial Chemistry, 1st ed; Wiley-VCH: New York, 2002; vol. 1.
2. Recent reviews on SPOS: Guillier, F.; Orain, D.; Bradley, M. Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry. Chem. Rev. 2000, 100, 2091-2158;
3. Blaney, P.; Grigg, R.; Sridharan, V. Traceless solid-phase organic synthesis. Chem. Rev. 2002, 102, 2607-2624. (Pubitemid 35377637)
4. Drioli, S.; Felluga, F.; Forzato, C.; Nitti, P.; Pitacco, G.; Valentin, E. Synthesis of (+)-and (-)-phaseolinic acid by combination of enzymatic hydrolysis and chemical transformations with revision of the absolute configuration of the natural product. J. Org. Chem. 1998, 63, 2385-2388; (Pubitemid 28188495)
5. Rodriguez, C. M.; Martin, T.; Martin, V. S. A new stereoselective synthesis of (-)-isoavenaciolide and (-)-avenaciolide. J. Org. Chem. 1996, 61, 8448-8452. (Pubitemid 26419358)
6. Grimm, E. L.; Reissig, H. U. 2-Siloxy-substituted methyl cyclopropanecarboxylates as building blocks in synthesis: Efficient one-pot conversion to γ-butyrolactones. J. Org. Chem. 1985, 50, 242-244;
7. Ghosh, A. K.; McKee, S. P.; Thompson, W. J. An efficient synthesis of hydroxyethylene dipeptide isosteres: The core unit of potent HIV-1 protease inhibitors. J. Org. Chem. 1991, 56, 6500-6503;
8. Askin, D.; Wallace, M. A.; Vacca, J. P.; Reamer, R. A.; Volante, R. P.; Shinkai, I. Highly diastereoselective alkylations of chiral amide enolates: New routes to hydroxyethylene dipeptide isostere inhibitors of HIV-1 protease. J. Org. Chem. 1992, 57, 2771-2773;
9. Koch, S. S. C.; Chamberline, A. R. Enantioselective preparation of β-alkyl-γ-butyrolactones from functionalized ketene dithioacetals. J. Org. Chem. 1993, 58, 2725-2737; (Pubitemid 23190124)
10. Lee, K.; Choi, Y.; Gullen, E.; Schlueter-Wirtz, S.; Schinazi, R. F.; Cheng, Y. C.; Chu, C. K. Synthesis and anti-HIV and anti-HBV activities of 20-fluoro-20,30-unsaturated l-nucleosides. J. Med. Chem. 1999, 42, 1320-1328. (Pubitemid 29181154)
11. Cardillo, G.; Orena, M. Stereocontrolled cyclofunctionalizations of double bonds through heterocyclic intermediates. Tetrahedron 1990, 46, 3321-3408;
12. Robin, S.; Rousseau, G. Electrophilic cyclization of unsaturated amides. Tetrahedron 1998, 54, 13681-13736; (Pubitemid 28500072)
13. Ranganathan, S.; Muraleedharan, K. M.; Vaish, N. K.; Jayaraman, N. Halo-and selenolactonisation: The two major strategies for cyclofunctionalisation. Tetrahedron 2004, 60, 5273-5308; (Pubitemid 38692714)
14. Blot, V.; Reboul, V.; Metzner, P. Asymmetric induction of the iodolactonization reaction of α-sulfurated γ-unsaturated amides. J. Org. Chem. 2004, 69, 1196-1201; (Pubitemid 38233400)
15. Breitenstein, K.; Llebariab, A.; Delgado, A. A solid-phase version of the Nozaki-Hiyama allylation of aldehydes with supported allylic bromides. Tetrahedron Lett. 2004, 45, 1511-1513; (Pubitemid 38134340)
16. Kabalka, G. W.; Venkataiah, B.; Chen, C. Baylis-Hillman Chemistry: Synthesis of cis-and trans-α-methylene-γ-lactones. Tetrahedron Lett. 2006, 47, 4187-4189;
17. Liu, H. J.; Tan, C. H. Iodobenzene-catalysed iodolactonisation using sodium perborate monohydrate as oxidant. Tetrahedron Lett. 2007, 48, 8220-8222;
18. Garnier, J. M.; Robin, S.; Rousseau, G. An approach to enantioselective 5-endo halo-lactonization reactions. Eur. J. Org. Chem. 2007, 3281-3291;
19. 2)-catalysed iodo-cyclisation of alkenes and alkynes using molecular oxygen. Tetrahedron Lett. 2008, 49, 4424-4426.
20. Nicolaou, K. C. Organoselenium-induced cyclizations in organic synthesis. Tetrahedron 1981, 37, 4097-4109;
21. Mellegaard, S. R.; Tunge, J. A. Selenium-catalyzed halolactonization: Nucleophilic activation of electrophilic halogenating reagents. J. Org. Chem. 2004, 69, 8979-8981. (Pubitemid 39603070)
22. Michels, R.; Kato, M.; Heitz, W. Polymere reagenzien 5*, polymerereagenzien. Makromol. Chem. 1976, 177, 2311-2318.
23. Nicolaou, K. C.; Pastor, J.; Barluenga, S.; Winssinger, N. Polymer-supported selenium reagents for organic synthesis. Chem. Commun. 1998, 1947-1948; (Pubitemid 128675863)
24. Ruhland, T.; Andersen, K.; Pedersen, H. Selenium-linking strategy for traceless solid-phase synthesis: Direct loading, aliphatic C-H bond formation upon cleavage, and reaction monitoring by gradient MAS NMR spectroscopy. J. Org. Chem. 1998, 63, 9204-9211; (Pubitemid 29008980)
25. Yanada K., Fujita T., Yanada R. Reduction of selenium with BER in methanol: Application to synthesis of dialkyl selenides. Synlett 1998, 971-972; (Pubitemid 128693952)
26. Zaragoza, F. New sulfur-and selenium-based traceless linkers-More than just linkers? Angew. Chem. Int. Ed. 2000, 39, 2077-2079; (Pubitemid 30435591)
27. Uehlin, L.; Wirth, T. Novel polymer-bound chiral selenium electrophiles. Org. Lett. 2001, 3, 2931-2933; (Pubitemid 33627227)
28. Fujita, K. I.; Hashimoto, S.; Oishi, A.; Taguchi, Y. Intramolecular oxyselenenylation and deselenenylation reactions in water, conducted by employing polymer-supported arylselenenyl bromide. Tetrahedron Lett. 2003, 44, 3793-3795; (Pubitemid 36428737)
29. Berlin, S.; Ericsson, C.; Engman, L. Radical carbonylation=reductive cyclization for the construction of tetrahydrofuran-3-ones and pyrrolidin-3-ones. J. Org. Chem. 2003, 68, 8386-8396; (Pubitemid 37329096)
30. Mogemark, M.; Gustafsson, L.; Bengtsson, C.; Elofsson, M.; Kihlberg, J. A fluorinated selenide linker for solid-phase synthesis of n-pentenyl glycosides. Org. Lett. 2004, 6, 4885-4886;
31. Cohen, R. J.; Fox, D. L.; Salvatore, R. N. A novel and highly efficient synthetic route to unsymmetrical organoselenides using cesium bases. J. Org. Chem. 2004, 69, 4265-4268; (Pubitemid 38736492)
32. Barrero, A. F.; Quílez del Moral, J. F.; Herrador, M. M.; Herrador, M. M.; Cortés, M.; Arteaga, P.; Catalán, J. V.; Sánchez, E. M.; Arteaga, J. F. Solid-phase selenium-catalyzed selective allylic chlorination of polyprenoids: Facile syntheses of biologically active terpenoids. J. Org. Chem. 2006, 71, 5811-5814; (Pubitemid 44117039)
33. Cao, J.; Huang, X. Solid-phase synthesis of bis-heterocyclic compounds with skeletal diversity from resin-bound 3-propargylamino-2-seleno-ester. J. Comb. Chem. 2010, 12, 1-4.
34. Sheng, S. R.; Xin, Q.; Liu, X. L.; Sun, W. K.; Guo, R.; Huang, X. Traceless solid-phase synthesis of 3-substituted isoxazoles and 3-substituted 5-iodoisoxazolines using polystyrene-supported vinyl selenide. Synthesis 2006, 2293-2296. (Pubitemid 44146975)
35. Sheng, S. R.; Hu, M. G.; Wu, D.; Cai, M. Z.; Huang, X. Solid-phase synthesis of 2-iodomethyl-2,3-dihydrobenzofurans using recyclable polymer-supported selenium bromide. Lett. Org. Chem. 2009, 6, 345-348.
36. Fu, G. Y.; Sheng, S. R.; Liu, X. L.; Cai, M. Z.; Huang, X. Solid-phase synthesis of vinyl-substituted 1,3,4-oxadiazoles using polymer-bound α-selenopropionic acid. Synth. Commun. 2008, 38, 4240-4249.
37. Batterby, A. R.; Westwood, S. W. Synthetic studies relevant to biosynthetic research on vitamin B12, part 5: Synthesis of (RS)-ring-B imide. J. Chem. Soc., Perkin Trans. 1987, 1, 1679-1687.
38. Kuhne, M. E.; Kuniewicz, J. F. O.; Kirkemo, C. L.; Bohnert, J. C. Studies in biomimetic alkaloid syntheses. Total syntheses of the C-14 epimeric hydroxyvincadifformines, tabersonine, a (hydroxymethy1)-d-norvincadifformine, and the C-20 epimeric pandolines 8. J. Org. Chem. 1982, 47, 1335-1343.
39. Kim, D. H.; Li, Z.-H.; Lee, S. S.; Park, J.; Chung, S. J. A novel tape of structurally simple nonpeptide inhibitors for α-chymotrypsin: Induced-fit binding of methyl 2-allyl-3-benzene-propanoate to the S2 subsite pocket. Bioorg. Med. Chem. 1998, 6, 239-249. (Pubitemid 28260939)
40. Rudler, H.; Harris, P.; Parlier, A.; Cantagrel, F.; Bellassoued, M.; Vaissermann, J. Transition-metal-catalyzed synthesis of d-hydroxy-γ- lactones from bis(trimethylsilyl) ketene acetals and allylic acetates via γ-unsaturated carboxylic acids. Comments on the formation of α-cyclopropyl carboxylic acids. J. Organomet. Chem. 2001, 624, 186-202. (Pubitemid 33667971)
41. Miller, M.; Goelitz, P. An efficient and general synthesis of 5-substituted pyrrolidinones. J. Org. Chem. 1981, 46, 1616-1618.
42. Negishi, E.; Coperet, C. Palladium-catalyzed highly diastereoselective cyclic carbopalladation-carbonylative esterification tandem reaction of iododienes and iodoarylalkenes. Org. Lett. 1999, 165-168.
43. Handa, S.; Jones, K.; Newton, C. G. Rotational energy barrier of the polarized carbon-carbon double bond in 3-(4-dimethylaminobenzylidene)pentane-2, 4-dione. Tetrahedron Lett. 1988, 29, 3841-3842.
44. 2 using an organotelluride catalyst. Org. Lett. 2001, 3, 349-352. (Pubitemid 33692992)
45. Tamru, Y.; Mizutani, M.; Furukawa, Y.; Kawamura, S.; Yoshida, Z.; Yanagi, K.; Minobe, M. 1,3-Asymmetric induction: Highly stereoselective synthesis of 2,4-transdisubstituted γ-butyrolactones and γ-butyrothiolactones. J. Am. Chem. Soc. 1984, 106, 1079-1085.
46. Arnold, R. T.; Lindsay, K. L. Participation of a neighboring carboxyl group in addition reactions, 11: The reaction of cyanogen iodide with γ,δ-unsaturated acids. J. Am. Chem. Soc. 1953, 75, 1048-1049.
47. Haas, J.; Piguel, S.; Wirth, T. Reagent-controlled stereoselective iodolactonizations. Org. Lett. 2002, 4, 297-300.