Application of cross metathesis in diene and polyene synthesis

Current Organic Synthesis

Volumn 10, Issue 1, 2013, Pages 43-66

  Wojtkielewicz, Agnieszka ^a  

^a UNIVERSITY OF BIALYSTOK   (Poland)

Author keywords

Cross metathesis; Cross coupling; Diene; Enyne metathesis; Olefin metathesis; Polyene; Synthetic methods; Tandem reaction

Indexed keywords

EID: 84873158280     PISSN: 15701794     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017913804810942     Document Type: Review

References (93)

1. For recent general reviews on olefin metathesis see:
2. Furstner, A. Olefin metathesis and beyond. Angew. Chem. Int. Ed., 2000, 39, 3012-3043;
3. Grubbs, R.H. Olefin metathesis. Tetrahedron, 2004, 60, 7117-7140;
4. Astruc, D. The metathesis reactions: from a historical perspective to recent developments. New J. Chem., 2005, 29, 42-56;
5. Herndon, J.W. The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2007. Coordination Chemistry Review, 2009, 253, 1517-1595.
6. Schrock, R.R.; Murdzek, J.S.; Bazan, G.C.; Robbins, J.; DiMare, M.; O'Reagan, M. Synthesis of molybdenum imido alkylidene complexes and some reactions involving acyclic olefins. J. Am. Chem. Soc. 1990, 112, 3875-3886;
7. Grubbs, R.H.; Trnka, T.M. The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story. Acc. Chem. Res., 2001, 34, 18-29;
8. Hoveyda, A.H.; Gillingham, D.G.; Van Veldhuizen, J.J.; Kataoka, O.; Garber, S.B.; Kingsbury, J.S.; Harrity, J.P.A. Ru Complexes bearing bidentate carbenes: from innocent curiosity to uniquely effective catalysts for olefin metathesis. Org. Biomol. Chem., 2004, 2, 8-23;
9. Schroni, Y.; Pederson, R.L. Evolution and applications of second-generation ruthenium olefin metathesis catalysts. Aldrichimica Acta, 2007, 40, 45-52.
10. Mol, J.C. Industrial applications of olefin metathesis. Journal of Molecular catalysis A: Chemical, 2004, 213, 39-45.
11. Chatterjee, A.K.; Choi, T.L.; Sanders, D.P.; Grubbs, R.H. A general model for selectivity in olefin cross metathesis. J. Am. Chem. Soc., 2003, 125, 11360-11370.
12. Gibson, S.E.; Keen, S.P. Cross-metathesis. Top. Organomet. Chem., 1998, 155-188.
13. Connon, S.J.; Blehert, S. Recent developments on olefin cross-metathesis. Angew. Chem. Int. Ed., 2003, 42, 1900-1923.
14. Vernall, A.J.; Abel, A.D. Cross metathesis of nitrogen-containing system. Aldrichimica Acta, 2003, 3, 93-105.
15. Nicolaou, K.C.; Bulger, P.G.; Sarlah, D. Metathesis reactions in total synthesis. Angew. Chem. Int. Ed. 2005, 44, 4490-4527.
16. Prunet, J. Application of olefin cross-metathesis to the synthesis of biologically active natural products. Top. Organomet. Chem., 2005, 5, 1559-1577.
17. Mori, M. Enyne metathesis. Top. Organomet. Chem. 1998, 133-154.
18. Poulsen, S.C.; Madsen, R. Enyne metathesis catalyzed by ruthenium carbene complexes. Synthesis, 2003, 1-18.
19. Diver, S.T.; Giessert, A.J. Enyne metathesis (enyne bond reorganization). Chem. Rev., 2004, 104, 1317-1382.
20. Fischmeister, C.; Bruneau, C. Ene-yne cross-metathesis with ruthenium carbene catalysts. Beilstein J. Org. Chem., 2011, 7, 156-166.
21. Morzycki, J.W. Application of olefin metathesis in the synthesis of steroids. Steroids 2011, 76, 949-966.
22. Rappoport, Z. The Chemistry of Dienes and Polyenes; John Wiley & Sons: Chichester, UK, 1997; Vol. 1
23. Rappoport, Z. The Chemistry of Dienes and Polyenes; John Wiley & Sons: Chichester, UK, 2001; Vol. 2.
24. Rockack, J., Ed.; Leukotrienes and Lipoxygenase, Elsevir, New York 1989;
25. Geern, R.H.; Lambeth, P.F. Leukotrienes. Tetrahedron, 1983, 39, 1687-1721.
26. Omura, S.; Tanaka, H. In: Macrolide antibiotics: Chemistry, Biology and Pratice;. Omura, S., Ed.; Academic Press, New York 1984, pp. 351-404;
27. Semlyen, J.A. Large Ring Molecules, Wiley, Chichester, 1996;
28. Rychnovsky, S.D. Oxo polyene macrolide antibiotics. Chem. Rev., 1995, 95, 2021-2040.
29. Isler, O., Ed., Carotenoids, Birkhauser, Basel, 1971, pp. 932;
30. Britton, G.; Goodwin, T.W.; Carotenoid Chemistry and Biochemistry Pergamon Press, Oxford, 1982, pp. 224.
31. Walter, M.H.; Floks, D.S.; Strack, D. Apocarotenoids: hormones, mycorrhizal metabolites and aroma volatiles. Planta, 2010, 232, 1-17.
32. Fishkin, N.; Berova, N.; Nakanishi, K. Primary events in dim light vision: a chemical and spectroscopic approach toward understanding protein/ chromophore interactions in rhodopsin. Chem Rec. 2004, 4, 120-135;
33. Gudas, L.J. Retinoids and vertebrate development. J. Biol. Chem., 1994, 269, 15399-15402;
34. Mark, M.; Ghyselinck, N.B.; Chambon, P. Functions of retinoid nuclear receptors in mouse embryonic development: lessons from genetic and pharmacological dissections of their signaling pathway. Annu. Rev. Pharmacol. Toxicol., 2006, 46, 451-480;
35. Chambon, P. A decade of molecular biology of retinoic acid receptors. FASEB J. 1996, 10, 940-954;
36. Heyman, R.A.; Mangelsdorf, D.J.; Dyck, J.A.; Stein, R.B.; Eichele, G.; Evans, R.M.; Thaller, C. 9-cis retinoic acid is a high affinity ligand for the retinoid X receptor. Cell, 1992, 68, 397-406.
37. Royer F., Vilain C., Elkaim L., Grimaud L. Selective domino ring-closing metathesis - cross-metathesis reactions between enynes and electrondeficient alkenes. Org. Lett., 2003, 5, 2007-2009.
38. Cesati, R.R., III; de Armas, J.; Hoveyda, A.H. Enantioselective total Synthesis of erogorgiaene: applications of asymmetric Cu-catalyzed conjugate additions of alkylzincs to acyclic enones. J. Am. Chem. Soc., 2004, 126, 96-101.
39. Salim, S.S.; Bellingham, R.H.; Brown, R.C.D. One-Pot ring-closing metathesis - alkene cross metathesis reactions of sulfamide-linked enynes. Eur. J. Org. Chem., 2004, 800-806.
40. Kitamura, T.; Sato, Y.; Mori, M. Synthetic study of (+)-anthramycin using ring-closing enyne metathesis and cross metathesis. Tetrahedron, 2004, 60, 9649-9657.
41. Kummer, D.A.; Brenneman, J.B.; Martin, S.F. Domino intramolecular enyne metathesis/cross metathesis approach to the xanthanolides. Enantioselective synthesis of (+)-8-epi-xanthatin. Tetrahedron, 2006, 62, 11437-11449.
42. Boyer, F.D.; Dubois, J.; Thoret, S.; Dau, M-E. T.H.; Hanna, I. Synthesis and tubulin-binding properties of new allocolchicinoids. Bioorg. Chem., 2010, 38, 149-158.
43. Mori, M. Recent progress on enyne metathesis: its application to syntheses of natural products and related compounds. Materials, 2010, 3, 2087-2140;
44. Kim, C.H.; An, H.J.; Shin, W.K.; Yu, W.; Woo, S.K.; Jung, S.K.; Lee, E. Stereoselective synthesisof (-)-amphidinolide E. E. Chem. Asian J. 2008, 3, 1523-1534;
45. Kim, C.H.; An, H.J.; Shin, W.K.; Yu, W.; Woo, S.K.; Jung, S.K.; Lee, E. Total synthesis of (-)-amphidinolide E. Angew. Chem. Int. Ed. 2006, 45, 8019-8021.
46. Funk, T.W.; Efskind, J.; Grubbs, R.H. Chemoselective construction of substituted conjugated dienes using an olefin cross-metathesis protocol. Org. Lett., 2005, 7, 187-190.
47. Krishna, C.V.; Bhonde, V.R.; Devendar, A.; Maitra, S.; Mukkanti, K.; Iqbal, J. A cross metathesis strategy for the synthesis of highly functionalized conjugated cyanodienes: synthesis of the C3-C17 framework of (-)-borrelidin. Tetrahedron Lett., 2008, 49, 2013-2017.
48. Dewi, P.; Randl, S.; Blechert, S. Cross-metathesis of 1,3-dienes with electron- deficient olefins. Tetrahedron Lett., 2005, 46, 577-580.
49. Kong, J.R.; Cho, C.W.; Krische, M.J. Hydrogen-mediated reductive coupling of conjugated alkynes with ethyl (N-sulfinyl)iminoacetates: synthesis of unnatural -amino acids via rhodium-catalyzed CC bond forming hydrogenation. J. Am. Chem. Soc., 2005, 127, 11269-11276.
50. Ferrie, L.; Amans, D.; Reymond, S.; Bellosta, V.; Capdevielle, P.; Cossy, J. Chemoselective cross-metathesis reaction between electron-deficient 1,3- dienes and olefins. J. Organomet. Chem., 2006, 691, 5456-5465.
51. Amans, D.; Bellosta, V.; Cossy, J. Total synthesis of pseudotrienic acid B: a bioactive metabolite from Pseudomonas sp. MF 381-IODS. Angew. Chem. Int. Ed., 2006, 45, 5870-5874;
52. Amans, D.; Bellosta, V.; Cossy, J. Synthesis of two bioactive natural products: FR252921 and pseudotrienic acid B. Chem. Eur. J., 2009, 15, 3457-3473.
53. Cossy, J.; Tsuchiya, T.; Ferrie, L.; Reymond, S.; Kreuzer, T.; Colober, F.; Jourdain, P.; Marko, I.E. Efficient syntheses of the polyene fragments present in amphidinols. Synlett, 2007, 14, 2286-2288.
54. Moura-Letts, G.; Curran, D.P. Selective synthesis of (2Z,4E)-dienyl esters by ene-diene cross metathesis. Org. Lett., 2007, 9, 5-8.
55. Morita, A.; Kuwahara, S. Cross-metathesis approach to a (2E,4E)-dienoic acid intermediate for synthesis of elaiolide. Tetrahedron Lett., 2007, 48, 3163-3166.
56. Niggemann, J.; Bedorf, N.; Florke, U.; Steinmetz, H.; Gerth, K.; Reichenbach, H.; Holfe, G. Spirangien A and B, highly cytotoxic and antifungal spiroketals from the myxobacterium Sorangium cellulosum: isolation, structure elucidation and chemical modifications. Eur. J. Org. Chem., 2005, 5013-5018.
57. Jermacz, I.; Maj, J.; Morzycki, J.W.; Wojtkielewicz, A. GC-MS analysis of -carotene ethenolysis products and their synthesis as potentially active vitamin A analogues. Toxicol. Mechanisms and Methods, 2008, 18, 469-471.
58. Wojtkielewicz, A.; Maj, J.; Morzycki, J.W. Cross metathesis of -carotene with electron-deficient dienes. A direct route to retinoids. Tetrahedron Lett., 2009, 50, 4734-4737.
59. Wojtkielewicz, A.; Maj, J.; Dzieszkowska, A.; Morzycki, J.W. Cross metathesis approach to retinoids and other -apocarotenoids. Tetrahedron, 2011, 67, 6868-6875.
60. Kajikawa, Y.; Iguchi, N.; Katasumura, S. Olefin metathesis in carotenoid synthesis. Org. Biomol. Chem., 2009, 7, 4586-4589;
61. Fontan, N.; Dominguez, M.; Alvarez, R.; de Lera, A.R. Synthesis of C40-symmetrical fully conjugated Carotenoids by olefin metathesis. Eur. J. Org., 2011, 6704-6712;
62. Fontán, N.; Alvarez, R.; de Lera A.R. Stereoselective Synthesis by Olefin Metathesis and Characterization of -Carotene (7,8,7,8-tetrahydro- carotene). J. Nat. Prod., 2012, 75, 975-979.
63. Lopez-Sanchez, C.; Hernandez-Cervantes, C.; Rosales, A.; Alvarez-Corrol, M.; Munoz-Dorado, M.; Rodriguez-Garcia, I. A convenient cross-metathesis approach to trisporins. Tetrahedron, 2009, 65, 9542-9549.
64. Mitton-Fry, M.J.; Cullen, A.J.; Sammakia, T. The total synthesis of the oxopolyene macrolide RK-397. Angew. Chem. Int. Ed., 2007, 46, 1066-1070.
65. Katz, T.; Sivavec, T.M. Metal-catalyzed rearrangement of alkene-alkynes and the stereochemistry of metallacyclobutene ring opening. J. Am. Chem. Soc., 1985, 107, 737-738.
66. Ostrowski, S.; Mikus, A. Synthesis of porhyrin - acetylene and porphyrindiene building blocks for New dyads preparation. Heterocycles, 2005, 65, 2339-2346.
67. Kotha, S.; Mandal, K. Metathesis of a novel dienediyne system: a unique example involving the usage of in situ generated ethylene as cross-enyne metathesis partner. J. Organomet. Chem., 2007, 692, 4921-4927.
68. Kim, M.; Park, S.; Maifeld, S.V.; Lee, D. Regio- and stereoselective enyne cross metathesis of silylated internal alkynes. J. Am. Chem. Soc., 2004, 126, 10242-10243.
69. Park, S.; Kim, M.; Lee, D. Tandem sequence of cross metathesis - ringclosing metathesis reaction of alkynyl silyloxy-tethered enynes. J. Am. Chem. Soc., 2005, 127, 9410-9415.
70. Kim, M.; Lee, D. Boron-directed regio- and stereoselective enyne cross metathesis: efficient synthesis of vinyl boronate containing 1,3-dienes. Org. Lett., 2005, 7, 1865-1868.
71. Clark, D.A.; Basile, B.S.; Karnofel, W.S.; Diver, S.T. Enyne crossmetathesis with strained geminally-substituted alkenes: direct access to highly substituted 1,3-dienes. Org. Lett., 2008, 10, 4927-4929.
72. Clark, D.A.; Clark, J.R.; Diver, S.T. Alkenol - alkyne cross metathesis. Org. Lett., 2008, 10, 2055-2058.
73. Clark, D.A.; Kulkarni, A.A.; Kalbarczyk, K.; Schertzer, B.; Diver, S.T. Tandem enyne metathesis and Claisen rearrangement: a versatile approach to conjugated dienes of variable substitution patterns. J. Am. Chem. Soc., 2006, 128, 15632-15636.
74. Kulkarni, A.A.; Diver, S.T. Cycloheptadiene ring synthesis by tandem intermolecular enyne metathesis. Org. Lett., 2003, 5, 3463-3466.
75. Kulkarni, A.A.; Diver, S.T. Ring synthesis by stereoselective, methylene-free enyne cross metathesis. J. Am. Chem. Soc., 2004, 126, 8110-8811.
76. Ravalec, L.V.; Fischmeister, C.; Bruneau, C. First transformation of unsaturated fatty esters involving enyne cross-metathesis. Adv. Synt. Catal., 2009, 351, 1115-1122.
77. Stragies, R.; Schuster, M.; Blechert, S. A novel ruthenium-catalysed tandem diyne cycloisomerization - cross metathesis process. Chem. Comunn., 1999, 237-238.
78. Kim, M.; Miller, R.L.; Lee, D. Cross and ring-closing metathesis of 1,3- diynes: metallotropic [1,3]-shift of ruthenium carbenes. J. Am. Chem. Soc., 2005, 127, 12818-12819;
79. Van de Weghe, P.; Bisseret, P.; Blanchard, N.; Eustache, J. Metathesis of heteroatom-substituted olefins and alkynes: current scope and limitations. J. Organomet. Chem., 2006, 691, 5078-5108.
80. Kotha, S.; Meshram, M.; Tiwari, A. Advanced approach to polycyclics by synergistic combination of enyne metathesis and Diels-Alder reaction. Chem. Soc. Rev., 2009, 38, 2065-2092.
81. Mix, S.; Blechert, S. Synthesis of cis-fused carbo-bicycles by domino enyne cross-metathesis/intramolecular Diels-Alder reaction. Org. Lett., 2005, 7, 2015-2018.
82. Kaliappan, K.P.; Ravikumar, V.; Pujari, S.A. Synthesis of a bicyclo[ 5.3.1]undecene by a facile domino enyne cross-metathesis/IMDA. Tetrahedron Lett., 2006, 47, 987-984.
83. Castagnolo D., Botta, L.; Botta, M. Stereoselective protecting group free synthesis of D,L-gulose ethyl glycoside via multicomponent enyne cross metathesis - hetero Diels-Alder reaction. Carbohydrate Res., 2009, 344, 1285-1288.
84. Castagnolo, D.; Botta, L.; Botta, M. One-pot multicomponent synthesis of 2,3-dihydropyrans: new access to furanose-pyranose 1,3-C-C-linkeddisaccharides. Tetrahedron Lett., 1998, 50, 1526-1528.
85. Kotha, A.; Mandal, K.; Banerjee, S.; Mobin, S. M. Synthesis of novel quinone- amino acid hybrids via cross-enyne metathesis and Diels-Alder reaction as key steps. Eur. J. Org. Chem., 2007, 1244-1255.
86. Kaliappan, K.P.; Subrahmanyam, A.V. A new versatile strategy for C-aryl glycosides. Org. Lett., 2007, 9, 1121-1124.
87. Pujari, S.A.; Kalliapan, K.P.; Valleix, A.; Gree, D.; Gree, R. A rapid access to new fluorinated 1,3-dienes and benzylic fluorides via metathesis on propargylic fluorides. Synlett, 2008, 16, 2503-2507.
88. Murelli, R.P.; Catalan, S.; Gannon, M.P.; Snapper, M.L. Rutheniumcatalyzed tandem enyne-cross metathesis - cyclopropanation: threecomponent access to vinyl cyclopropanes. Tetrahedron Lett., 2008, 49, 5714-5717.
89. Kalbarczyk, K.P.; Diver, S.T. Enyne metathesis/Brønsted acid-promoted heterocyclization. J. Org. Chem., 2009, 74, 219-2196.
90. Fujimura, O.; Honma, T. Olefination of aldehydes by ethyl diazoacetate catalyzed by a ruthenium(II) complex. Tetrahedron Lett., 1998, 39, 625-626.
91. Murelli, R.P.; Snapper, M.L. Ruthenium-catalyzed tandem crossmetathesis/ Wittig olefination: generation of conjugated dienoic esters from terminal olefins. Org. Lett., 2007, 9, 1749-1752.
92. Bonini, C.; Chiummiento, L.; Videtta, V.; Colobert, F.; Solladic, G. A concise and efficient stereoselective synthesis of the C1-C11 fragment of Macrolactin A. Synlett, 2006, 15, 2427-2430.
93. BouzBouz, S.; Roche, C.; Cossy, J. Simple synthesis of conjugated all-(E)- polyenic aldehydes, ketones, and esters using chemoselective crossmetathesis and an iterative sequence of reactions: application to the synthesis of novenone B. Synlett, 2009, 5, 803-807.