Iodocyclization: Past and present examples

Current Organic Chemistry

Volumn 15, Issue 7, 2011, Pages 1058-1080

  Banerjee, Ajoy K ^a   Laya, Manuel S ^a   Cabrera, Elvia V ^b  

^a INSTITUTO VENEZOLANO DE INVESTIGACIONES CIENTÍFICAS   (Venezuela)

^b FACULTAD DE CIENCIAS VETERINARIAS   (Venezuela)

Author keywords

Cyclization; Iodinated arenes; Iodine; Propargylic ester; fluorinated lactones

Indexed keywords

AROMATIC COMPOUNDS; ESTERS; FLUORINE COMPOUNDS; IODINE; KETONES;

ALLYLICS; CYCLIZATIONS; IODINATED ARENES; IODOCYCLIZATION; NATURAL BIOACTIVES; NATURAL PRODUCTS; PAST AND PRESENT; PROPARGYLIC ESTER; Β-FLUORINATED-Γ-LACTONE; Γ-LACTONE;

CYCLIZATION;

EID: 79952745775     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211794785109     Document Type: Review

References (64)

1. Togo, H.; Iida, S. Synthetic use of molecular iodine for organic synthesis. Synlett, 2006, 6, 2159.
2. Banerjee, A. K.; Vera, W.; Mora, H.; Laya, M. S.; Bedoya, L.; Cabrera, E. V. Iodine in organic sintesis. J. Sci. Ind. Res., 2006, 65, 299.
3. Laya, M. S.; Banerjee, A. K.; Cabrera, E.V. Iodolactonization: past and present examples. Curr. Org. Chem., 2009, 13, 720.
4. Jung, M. E. A review on annulation. Tetrahedron, 1976, 32, 3.
5. Sauer, J. Diels-Alder Reactions. New Preparative aspects. Angew. Chem. Int. Ed., 1966, 5, 211.
6. Sauer, J. Diels-Alder Reactions. Reaction Mechanisms. Angew. Chem. Int. Ed. 1967, 6, 16.
7. Schaefer, J. P.; Bloomfield, J. L. The Dieckmann condensation. Org. Reactions., 1959, 15, 3.
8. Pellissier, H. Recent developments in the Nazarov process. Tetrahedron., 2005, 61, 6479.
9. Frederickson, M.; Grigg, R. Electrophile mediated heteroatom cyclizations onto C-C π-bonds. Part1. Halogen and chalcogen mediated cyclization. Org. Prep. Proc. Int., 1997, 29, 33.
10. Rychnovsky, S. D.; Bartlet, P. A. Stereocontrolled synthesis of cis 2,5-diinfstituted tetrahydrofurans and cis- and-linalyl oxides. J. Am. Chem. Soc., 1981, 103, 3963.
11. Bartlett, P. A.; Holmes, C. P. A highly stereoselective synthesis of davanone. Tetrahedron Letts., 1983, 24, 1365.
12. Honda, Y.; Ori, A.; Tsuchihashi, G-I. Stereoselective synthesis of (+) davanone and (+) artemone via anti-selective epoxidation and iodocyclization. Chem. Letts., 1987, 1259.
13. Marek, I.; Lefrancois, J. M.; Normant, J. F. Iodocyclization of olefinic tertbutyl ethers: an easy stereocontrolled synthesis of cis-infstituted tetrahydrofurans. Tetrahedron Letts., 1992, 33, 1747.
14. Boivin Taryn, L. B. Synthetic routes to tetrahydrofuran, tetrahydropyran, and spiroketal units of polyether antibiotics and a survey of spiroketals of other natural products. Tetrahedron, 1987, 43, 3309.
15. Semple, J. E.; Joullie, M. M. Synthesis of reduced furans and 3(2H)-dihydrofuranones with manipulable functionality. Heterocycles, 1980, 14, 1825.
16. Kitagawa, O.; Inoue, T.; Hirano, K.; Taguchi, T. Ionic iodocarbocyclization reactions of 4-alkenyl- and 4-alkynylmalonate derivatives. J. Org. Chem., 1993, 58, 3106.
17. Curran, D. P.; Chang, C. T. Atom transfer cyclization reactions of alpha-iodo esters, ketones and malonates. Examples of selective 5-oxo, 6-endo, 6-exo and 7-endo ring closures. J. Org. Chem., 1989, 54, 3140.
18. Laurie, D.; Lucas, E.; Nonhebel, D. C.; Suckling, C. J.; Walton, J. C. Mechanism of hydrogen transfer by nicotinamide coenzymes and some dehydrogenases. Tetrahedron, 1986, 42, 1035.
19. Nonhebel, D. C.; Suckling, C. J.; Walton, J. C. The influence of trialkylsilyoxy groups on the rate of ring opening cyclopropylmethyl radicals. Tetrahedron Letts., 1982, 23, 4477.
20. Suckling, C. J. The Cyclopropyl group in studies of enzyme mechanism and inhibition. Angew. Chem. 1988, 100, 555.
21. Fournet, G.; Balme, G.; Gore, J. Synthesis of (E)-arylidene- and allylidenecyclopentanes by a palladium(0) complex catalyzed annulation Tetrahedron, 1991, 47, 6293.
22. Barks, J. M.; Knight, D. W.; Weingarten, G. G. A stereoelective approach to annulated tetrahydrofurans by iodocyclisations of 2-alkenylcycloalkan-1-ols. Chem. Communs., 1994, 719.
23. Kang, S. H.; Lee, S. S.; Park, C. M. Catalytic enantioselective iodocyclization of γ- hydroxyl-cis- alkene. J. Am. Chem. Soc., 2003, 125, 15748.
24. Antonioletti, R.; Malancona, S.; Cattaruzza, F.; Bovicelli, P. Iodoenolcyclisation of 2(1,3-diinfstituted -1-allyl)-1,3-dicarbonyl compounds: diastereoselective syntesis of tetrainfstituted dihydrofurans. Tetrahedron, 2003, 59, 1673.
25. Antonioletti, R.; Malancona, S.; Bovicelli, P. Iodoenolcyclization of 2-allyl infstituted _-keto esters under thermodynamic conditions. Heterocycles, 2004, 63, 1573.
26. Antonioletti, R.; Malancona, S.; Bovicelli, P. Diastereoselective synthesis of 4,5-dihydrofurans by iodoenolcyclisation of 2-allyl-1,3-dicarbonnyl compounds. Tetrahedron, 2002, 58, 8825.
27. Bartlett, P. A.; Myerson, J. Stereoselective epoxidation of acyclic olefinic carboxylic acids via iodolactonization. J. Am. Chem. Soc. 1978, 100, 3950.
28. Ek, F.; Wistrand, L-G.; Frejd, T. Synthesis of fused tetrazole and imidazole derivatives via iodocyclization. Tetrahedron, 2003, 59, 6759.
29. Sabate, M.; Llebaria, A.; Molins, E.; Miravitlles, C.; Delgado, A, Iodocyclization of O-3-cyclohexenyl) thiocarbamidates. An unexpexted approach to vicinal cis-aminocyclohexenols. J. Org. Chem. 2000, 65, 4826.
30. Saito, T.; Horikoshi, T.; Otani, T.; Matsuda, Y.; Karakasa, T. A facile and efficient one-pot synthesis of thiochromans from bis(2-formylphenyl) disulfide and alkenols via iodine-promoted generation and infsequent intramolecular cycloaddition of ortho-thio-benzoquinone methides. Tetrahedron Letts., 2003, 44, 6513.
31. Roy, B. G.; Roy, A.; Achari, B.; Mandal, S. B. A single pot entry to cyclic ethers of varied ring sizes from diols via phosphonium ion induced iodination and base catalyzed Williamson etherification. Tetrahedron Letts. 2006, 47, 7783.
32. de Armas, P.; Concepcion, J.I.; Francisco, C.G.; Hernandez, R.; Salazar, J. A.; Suarez, E. Intramolecular hydrogen abstraction hypervalent organoiodine compounds, convenient reagents for alkoxy radical reaction. J. Chem. Soc. Perkin Trans. I, 1989, 405.
33. Banerjee, A. K.; Hurtado, H.; Laya, M.; Acevedo, J. C.; Alvarez, J. Total synthesis of (±)Pisiferic acid. J. Chem. Soc. Perkin Trans. I, 1988, 931.
34. Banerjee, A. K.; Matheud, C. A. P.; Hurtado, H. E.; Diaz, M. G. Synthesis of (±) -1β- Methoxy-9β,7β-epoxy-5β-methyl-trans decalin. Heterocycles, 1986, 24, 2155.
35. Banerjee, A. K.; Hurtado, H. E.; Carrasco, M. C. Synthetic studies leading to the total synthesis of eudesmane sesquiterpenes. J. Chem. Soc. Perkin Trans. I. 1982, 2547.
36. Banerjee, A. K. Synthesis of cyclic ethers and their utility in the synthesis of terpenoid compounds. J. Sci. Ind. Res. 1996, 55, 915.
37. Stefani, H. A.; Petragnani, N.; Valduga, C. J.; Brandt, C. A. Iodine promoted cyclofunctionalization reaction of 2,4-dialkenyl-1,3-dicarbonyl compounds. Tetrahedron Letts. 1997, 38, 4977.
38. Arnold, R. T.; Lindsey, K. L. Participation of a neighbouring carboxyl groups in addition reactions. The reaction of cyanogens iodide with γ, δ -unsaturated acids. J. Am. Chem. Soc., 1953, 75, 1048.
39. Do Amaral, A. T.; El Seoud, O. A.; Do Amaral, L. Effects of α infstitution on the rate of chloromercuriolactonization of effects of γ, δ -unsaturated acids. J. Org. Chem. 1975, 40, 2534.
40. Ansell, M. F.; Palmer, M. H. The cyclisation of olefinic acids to ketones and lactones. Quat. Revs. 1964, 211.
41. Tredwell, M.; Luft, J. A. R.; Schuler, M.; Tenza, K.; Houk, K. N.; Gouverneur, V. Fluorine-Directed diastereoselective iodo-cyclizations. Angew. Chem. Int. Ed. 2008, 47, 357.
42. Kim, I.; Choi, J.; Won, H. K.; Lee, G. H. Expeditious synthesis of indolizine derivatives via iodine mediated 5-endo-dig cyclization. Tetrahedron Letts. 2007, 48, 6863
43. Tsuji, J. Palladium Reagents and Catalysts: New Perspective for the 21st Century, Wiley-VCH, Weinheim, Germany, 2004.
44. Jeffery, T. Highly stereospecific palladium-catalyzed vinylation of vinylic halides under solid-liquid phase transfer conditions. Tetrahedron Letts. 1985, 26, 2667.
45. Renaud, P.; Sibi, M.P. Radicals in Organic Synthesis. Wiley-VCH, Weinheim, Germany, 2001.
46. Curran, D; Porter, N.A.; Giese, B. Stereochemistry of Radical Reactions. Wiley-VCH, Weinheim, Germany, 1995.
47. Choi, J.; Lee, G. H.; Kim, I. Efficient synthesis of highly infstituted indolizinones via iodocyclization and 1,2-shift. Synlett. 2008, 1243.
48. Baldwin, J. E. Rules for ring closure. Chem. Communs. 1976, 734.
49. Matsumoto, S.; Takase, K.; Ogura, K. Novel formation of iodobenzene derivatives from 1-(methylthio)-3-tosylhexa-1,3-dien-5-ynes via iodineinduced intramolecular cyclization. J. Org. Chem. 2008, 73, 1726.
50. Martin, R.; Cuenca, A.; Buchwald, S. L. Sequential copper-catalyzed Vinylation/ cyclization: an efficient synthesis of functionalized oxazoles. Org. Letts. 2007, 9, 5521.
51. Singh, P.; Bhardwaj, A.; Kaur, S.; Kumar. S. Design, synthesis and evaluation of tetrahydropyran based COX-1/2 inhibitors. Eur. J. Med. Chem. 2009, 44, 1278.
52. Lu, B.; Jiang, X.; Fu, C.; Ma, S. Highly regio and stereoselective cyclic iodoetherification of 4,5-alkadienols. An efficient preparation of 2-(1'(z)-iodoalkenyl)tetrahydrofurans. J. Org. Chem. 2007, 74, 438.
53. Jonasson, C.; Horvath, A.; Backvall, J. E. Intramolecular palladium(II)-catalyzed 1,2-addition to allenes. J. Am. Chem. Soc., 2000, 122, 9600.
54. Ma, S. Transition metal-catalyzed /mediated reaction of allenes with a nucleophilic functionality connected to the -carbon atom. Acc. Chem. Res., 2003, 36, 701.
55. Caupene, C.; Chaume, G.; Ricard, L.; Brigaud, T. Iodocyclization of chiral CF3-allylmorpholinones: a versatile strategy for the synthesis of enantiopure α-Tfm-prolines and α -Tfm-dihydroxyprolines. Org. Letts., 2009, 11, 209.
56. Chaume, G.; Van Severen, M. C.; Ricard, L.; Brigaud, T. Concise access to enantiopure (S)- and (R)-α-trifluromethylpyroglutamic acids from ethyl trifluropyruvate-based CF3 oxazolidines (FOX). J. Fluor. Chem., 2008, 129, 1104.
57. Chaume, G.; Van Severen, M. C.; Marinkovic, S.; Brigaud, T. Straightforward synthesis of (S) and (R)-α-trifluoromethyl praline from chiral oxazolidines derived from ethyl trifluropyruvate. Org. Letts., 2006, 8, 6123.
58. Deb, M.L.; Bhuyan, P.J. An efficient method for the synthesis of indolo[3,2-b]carbazoles from 3,3'-bis(indolyl)methanes catalyzed by molecular iodine. Synlett., 2008, 325.
59. Bradfield, C.A.; Bjeldanes, L.F. High-performance liquid chromatographic analysis of anticarcinogenic indoles in Brassica oleracea. J. Agric. Food. Chem. 1987, 35, 46.
60. Fukamachi, S.; Konishi, H.; Kobayashi, K. Synthesis of 2-benzothiophene-1(3H)-thione and isothiochromene-1-thione derivatives by iodine-mediated cyclization of lithium 2-(vinyl)dithiobenzoate derivatives. Heterocycles, 2009, 78, 169.
61. Murai, T.; Niwa, H.; Kimura, T.; Shibahara, F. Iodo-cyclization of Nhomoallyl thioamides leading to 2,4-diaryl-5,6-dihydro-4H-1,3-thiazines. Chem. Letts. 2004, 33, 508.
62. Jones, A. D.; Knight, D. W.; Hibbs, D. E. A stereochemically flexible approach to pyrrolidines based on 5-endo-trig-iodocyclisations of homoallylic sulfonamides. J. Chem. Soc. Perkin Trans. I. 2001, 1182.
63. Fiorelli, C.; Marchioro, C.; Martelli, G.; Monari, M.; Savoia, D. Iodinemediated cyclization of (4R,5R)-4,5-diamino-N,N-bis[(1S)-1-phenylethyl]-1,7-octadiene- A stereoselective route to 2,5-diazabicyclo[2.2.1]heptanes. Euro. J. Org. Chem. 2005, 3987.
64. Alvaro, G.; Di Fabio, R.; Gualandi, A.; Fiorelli, C.; Monari, M.; Savoia, D.; Zoli, L. Stereoselective synthesis of infstituted 2,5-diazabicyclo[2.2.1]-heptanes by iodine-mediated cyclization of optically pure compounds containing the 4,5-diamino-1,7-octadiene and 1,2-diamino-4-alkene moieties. Tetrahedron. 2009, 63, 12446.