Enabling access to diverse bioactive molecules through enyne metathesis concepts

Current Organic Chemistry

Volumn 17, Issue 22, 2013, Pages 2678-2720

  Dragutan, Ileana ^a   Dragutan, Valerian ^a   Demonceau, Albert ^b   Delaude, Lionel ^b  

^a ACADEMY OF ROMANIAN SCIENTISTS   (Romania)

^b UNIVERSITY OF LIÈGE   (Belgium)

Author keywords

Bioactive natural compounds; Cross metathesis; Enyne metathesis; Relay ring closing; Ring closing metathesis; Ring rearrangement metathesis; Ruthenium catalysts; Skeletal bond reorganization; Tandem processes

Indexed keywords

ADDITION REACTIONS; ALLYLATION; CATALYSIS; RUTHENIUM; SYNTHESIS (CHEMICAL);

BIOACTIVE NATURAL COMPOUNDS; CROSS METATHESIS; ENYNE METATHESIS; RELAY RING-CLOSING; REORGANISATION; RING CLOSING METATHESIS; RING CLOSINGS; RING RE-ARRANGEMENT METATHESIS; RUTHENIUM CATALYSTS; SKELETAL BOND REORGANIZATION; TANDEM PROCESS;

SCAFFOLDS;

EID: 84893193326     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/13852728113179990113     Document Type: Article

References (253)

1. Nicolaou, K.C.; Hale, C.R.H.; Nilewski, C.; Ioannidou, H.A. Constructing molecular complexity and diversity: Total synthesis of natural products of biological and medicinal importance, Chem. Soc. Rev. 2012, 41, 5185-5238.
2. Pandolfi, E.; Schapiro, V.; Heguaburu, V.; Labora, M. Enantioselective synthesis of natural epoxyquinoids. Curr. Org. Synth. 2013, 10, 2-42.
3. Xu, Y.-Y.; Liu, C.; Liu, Z.-P. Advances in the total synthesis of cyclodepsipeptide (+)-jasplakinolide (jaspamide) and its analogs, Curr. Org. Synth. 2013, 10, 67-89.
4. Kotora, M.; Hessler, F.; Eignerová, B. Transitionmetal-mediated or -catalyzed syntheses of steroids and steroid-like compounds, Eur. J. Org. Chem. 2012, 29-42.
5. Honda, T. Investigation of innovative synthesis of biologically active compounds on the basis of newly developed reactions. Chem. Pharm. Bull. 2012, 60(6) 687-705.
6. Kotha, S.; Meshram, M.; Tiwari, A. Advanced approach to polycyclics by a synergistic combination of enyne metathesis and Diels-Alder reaction. Chem. Soc. Rev. 2009, 38, 2065-2092.
7. Banti, D.; North, M. Totally atom economical tandem-metathesis and Diels-Alder approach to polycyclic compounds. Tetrahedron Lett. 2002, 43, 1561-1564.
8. Cossy, J.; Arseniyadis, S.; Meyer, C. Eds. Metathesis in Natural Product Synthesis, Wiley-VCH: Weinheim, Germany, 2010.
9. Nicolaou, K.C.; Bulger, P.G.; Sarlah, D. Metathesis reactions in total synthesis. Angew. Chem. Int. Ed. 2005, 44, 4490-4527.
10. Dragutan, I.; Dragutan, V.; Demonceau, A. Targeted drugs by olefin metathesis: piperidine-based iminosugars. RSC Adv. 2012, 2(3), 719-736.
11. Fürstner, A. Metathesis in total synthesis. Chem. Commun. 2011, 47, 6505-6511.
12. Meek, S.J.; O'Brien, R.V.; Llaveria, J.; Schrock, R.R.; Hoveyda, A.H. Catalytic Z-selective olefin crossmetathesis for natural product synthesis. Nature 2011, 471, 461-466.
13. Prunet, J.; Grimaud, L. Cross-metathesis in natural products synthesis. In: Metathesis in Natural Product Synthesis: Strategies, Substrates and Catalysts; Cossy, J.; Arseniyadis, S.; Meyer, C. Eds. Wiley-VCH: Weinheim, Germany, 2010; pp. 287-312.
14. Bicchielli, D.; Borguet, Y.; Delaude, L.; Demonceau, A.; Dragutan, I.; Dragutan, V.; Jossifov, C.; Kalinova, R.; Nicks, F.; Sauvage, X. Recent applications of alkene metathesis in fine chemical synthesis. In: Green Metathesis Chemistry - Great Challenges in Synthesis, Catalysis and Nanotechnology. NATO Science for Peace and Security Series - A: Chemistry and Biology Series; Dragutan, V.; Demonceau, A.; Dragutan, I.; Finkelshtein, E.Sh., Eds.; Springer: Dordrecht, 2010; pp. 207-274.
15. Love, J.A. Olefin metathesis strategies in the synthesis of biologically relevant molecules. In: Handbook of Metathesis; Grubbs, R.H., Ed.; WILEY-VCH: Weinheim, Germany, 2003; Vol. 2, pp. 296-315.
16. Tietze, L.F., Dufert, A. Multiple Pd-catalyzed reactions in the synthesis of natural products, drugs, and materials. Pure Appl. Chem. 2010, 82(7), 1375-1392.
17. Dounay, A.B., Overman, L.E. The asymmetric intramolecular Heck reaction in natural product total synthesis. Chem. Rev. 2003, 103, 2945-2963.
18. Tietze, L.F.; Brasche, G.; Gericke, K. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2006.
19. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
20. Tietze, L.F., Dufert, A. In: Catalytic Asymmetric Conjugate Reactions; Cordóva, A., Ed.; Wiley-VCH: Weinheim, Germany, 2010.
21. Hoveyda, A.H. Catalytic asymmetric olefin metathesis. In: Handbook of Metathesis; Grubbs, R.H., Ed.; WILEY-VCH: Weinheim, Germany, 2003; Vol. 2, pp. 128-150.
22. Donde, Y.; Overman, L. E. In: Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
23. Grubbs, R.H., Ed.; Handbook of Metathesis; Wiley-VCH: Weinheim, Germany, 2003.
24. Chauvin, Y. Olefin metathesis: The early days (Nobel lecture). Angew. Chem. Int. Ed. 2006, 45, 3741-3747.
25. Schrock, R.R. Multiple metal-carbon bonds for catalytic metathesis reactions (Nobel lecture). Angew. Chem. Int. Ed. 2006, 45, 3748-3759.
26. Grubbs, R.H. Olefinmetathesis catalysts for the preparation of molecules and materials (Nobel lecture). Angew. Chem. Int. Ed. 2006, 45, 3760-3765.
27. Schrock, R.R. Recent Advances in Olefin Metathesis Chemistry. Chemistry Today 2009, 27, 2-9.
28. Astruc, D.; Diallo, A.K.; Gatard, S.; Liang, L.; Ornelas, C.; Martinez, V.; Méry, D.; Ruiz, J. Olefin metathesis in nano-sized systems. Beilstein J. Org. Chem. 2011, 7, 94-103.
29. Dragutan, V.; Dragutan, I.; Delaude, L.; Demonceau, A. Exploring new achievements in olefin metathesis catalysts: Part 1 - Highlights on N-heterocyclic carbene ruthenium complexes. Chemistry Today 2009, 27, 9-12.
30. Dragutan, I.; Dragutan, V.; Delaude, L.; Demonceau, A. Exploring new achievements in olefin metathesis catalysts: Part 2 - Compelling innovations in ruthenium complexes. Chemistry Today 2009, 27, 13-16.
31. Nolan, S.P.; Clavier, H. Chemoselective olefin metathesis transformations mediated by ruthenium complexes. Chem. Soc. Rev. 2010, 39, 3305-3316.
32. Astruc, D. The olefin metathesis reactions in dendrimers. In: Green Metathesis Chemistry - Great Challenges in Synthesis, Catalysis and Nanotechnology. NATO Science for Peace and Security Series - A: Chemistry and Biology Series; Dragutan, V.; Demonceau, A.; Dragutan, I.; Finkelshtein, E.Sh., Eds.; Springer: Dordrecht, 2010; pp. 173-184.
33. Zuercher, W.J.; Scholl, M.; Grubbs, R.H. Ruthenium-catalyzed polycyclization reactions. J. Org. Chem. 1998, 63, 4291-4298.
34. Dragutan, V.; Dragutan, I.; Balaban, A.T. Metathesis catalysed by the platinum group metals. A new strategy for the synthesis of organic compounds and polymers. Part III: Acyclic diene metathesis reactions and ring-opening metathesis polymerizations. Platinum Metals Rev. 2000, 44(4), 168-172.
35. Grubbs, R.H. Olefin metathesis. Tetrahedron 2004, 60, 7117-7140.
36. Testero S.A.; Mata, E.G. Synthesis of 3-(aryl)alkenyl-l-lactams by an efficient application of olefin cross-metathesis on solid support, Org. Lett. 2006, 8, 4783-4786.
37. Poeylaut-Palena, A.A.; Mata, E.G. Unravelling the olefin cross metathesis on solid support. Factors affecting the reaction outcome, Org. Biomol. Chem. 2010, 8, 3947-3956.
38. Wojtkielewicz, A. Application of cross metathesis in diene and polyene synthesis. Curr. Org. Synth. 2013, 10, 43-66.
39. Hoveyda, A.H.; Zhugralin, A.R. The remarkable metal-catalysed olefin metathesis reaction. Nature 2007, 450, 243-251.
40. Samojlowicz, C.; Bieniek, M.; Grela, K. Ruthenium-based olefin metathesis catalysts bearing N-heterocyclic carbene ligands. Chem. Rev. 2009, 109, 3708-3742.
41. Michalak, M.; Gulajski, L.; Grela, K. Alkene Metathesis. In: Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; de Meijere, A., Ed.; Georg Thieme Verlag KG, 2010; Vol. 47a (Alkenes), pp. 327-438.
42. Mitan, C.I.; Dragutan, V.; Dragutan, I. New insights into the mechanism of alkene metathesis. Rev. Roum. Chim. 2011, 56(4), 299-316.
43. Torborg, C.; Samojlowicz, C.; Grela, K. Metathesis Reactions. In: Science of Synthesis: Methods of Molecular Transformations; S. Kobayashi, Ed.; Georg Thieme Verlag KG, 2012; Vol. 2011/5: Water in Organic Synthesis, Section 3.6, pp. 225-256.
44. Grela, K.; Gulajski, L.; Skowerski, K. Alkene Metathesis in Water. In: Metal-Catalyzed Reactions in Water; Dixneuf, P.; Cadierno, V., Eds.; Wiley-VCH, 2013; Ch. 8, pp. 291-333.
45. Grela, K., Ed.; Progress in Metathesis Chemistry; Beilstein J. Org. Chem. 2010/2011, Vol. 6: 1089-1090.
46. Dragutan, V.; Demonceau, A.; Dragutan, I.; Finkelshtein, E.Sh., Eds.; Green Metathesis Chemistry - Great Challenges in Synthesis, Catalysis and Nanotechnology. NATO Science for Peace and Security Series - A: Chemistry and Biology Series; Springer: Dordrecht, 2010; pp. 425.
47. Dragutan, I.; Dragutan, V.; Mitan, C.; Vosloo, H.C.M.; Delaude, L.; Demonceau, A. Metathesis access to monocyclic iminocyclitol-based therapeutic agents. Beilstein J. Org. Chem. 2011, 7, 699-716.
48. Bicchielli, D.; Borguet, Y.; Delaude, L.; Demonceau, A.; Dragutan, I.; Dragutan, V.; Hans, M.; Jossifov, C.; Nicks, F.; Willem, Q. Olefin metathesis as key step in the synthesis of bioactive compounds. Challenges in the total synthesis of (-)-kendomycin, Curr. Org. Synth. 2012, 9(3), 397-405.
49. Demonceau, A.; Dragutan, I.; Dragutan, V.; Le Gendre, P. Olefin metathesis as key step in the synthesis of bioactive compounds: challenges in the total synthesis of iriomoteolides. Curr. Org. Synth. 2012, 9(6), 779-790.
50. Dragutan, I.; Dragutan, V.; Demonceau, A.; Vosloo, H.C.M. Synthesis of castanospermine and epimers by metathesis routes. Curr. Org. Chem. 2013, 17(22), 2721-2739.
51. Dassonneville, B.; Delaude, L.; Demonceau, A.; Dragutan, I.; Dragutan, V.; Etsé, K.S.; Hans, M. Selected recent advances in the synthesis of bioactive compounds with olefin metathesis as a key step. Curr.
52. Lee, Y.-J.; Schrock, R.R.; Hoveyda, A.H. Efficient endo-selective enyne ring-closing metathesis reactions promoted by stereogenic-at-Mo monoaryloxide complexes. Synthesis of cyclic dienes not accessible through reactions with Ru carbenes. J. Am. Chem. Soc. 2009, 131, 10652-10661.
53. Mori, M.; Kitamura, T. Ene-yne and alkyne metathesis. In: Comprehensive Organometallic Chemistry III, Transition Metal Organometallics in Organic Synthesis; Hiyama, T., Ed.; Elsevier: London, UK, 2005; pp. 271-310.
54. Poulsen, C.S.; Madsen, R. Enyne metathesis catalyzed by ruthenium carbene complexes. Synthesis, 2003, 1-18.
55. van Otterlo, W.A.L.; Lindani Ngidi, E.; de Koning, C.B.; Fernandes, M.A. Synthesis of dienynes from alkenes and diynes using ruthenium mediated ring-closing metathesis. Tetrahedron Lett. 2004, 45, 659-662.
56. Mori, M. Enyne metathesis. Top. Organomet. Chem. 1998, 1, 133-154.
57. Sashuk, V.; Ignatowska, J.; Grela, K. A fine-tuned molybdenum hexacarbonyl/ phenol initiator for alkyne metathesis. J. Org. Chem. 2004, 69, 7748-7751.
58. Schrock, R.R. The discovery and development of high oxidation state alkylidyne complexes for alkyne metathesis. In: Handbook of Metathesis; Grubbs, R.H. Ed., Wiley-VCH: Weinheim, Germany, 2003, Vol. 1, pp. 173-189.
59. Fürstner, A.; Mathes, C.; Lehmann, C.W. Alkyne metathesis: Development of a novel molybdenum-based catalyst system and its application to the total synthesis of epothilone A and C. Chem. Eur. J. 2001, 7, 5299-5317.
60. López, J.C.; Plumet, J. Metathesis reactions of carbohydrates: Recent highlights in alkyne metathesis. Eur. J. Org. Chem. 2011, 1803-1825.
61. Lehr, K.; Mariz, R.; Leseurre, L.; Gabor, B.; Fürstner, A. Total synthesis of tulearin C. Angew. Chem. Int. Ed. 2011, 50, 11373-11377.
62. Davies, P.V. Ring-closing alkyne metathesis in natural product synthesis. In: Metathesis in Natural Product Synthesis; Cossy, J.; Arseniyadis, S.; Meyer, C., Eds.; Wiley-VCH: Weinheim, 2010, pp. 205-223.
63. Mori M. Synthesis of natural products and related compounds using enyne metathesis. In: Metathesis in Natural Product Synthesis: Strategies, Substrates and Catalysts; Cossy, J; Arseniyadis S.; Meyer C., Eds; Wiley-VCH: Weinheim, 2010, pp. 183-204.
64. Chattopadhyay, S.K.; Karmakar, S.; Biswas, T.; Majumdar, K.C.; Rahaman, H.; Roy, B. Formation of medium ring heterocycles by diene and enyne metathesis. Tetrahedron 2007, 63, 3919-3952.
65. Villar, H.; Frings, M.; Bolm, C. Ring-closing enyne metathesis: A powerful tool for the synthesis of heterocycles. Chem. Soc. Rev. 2007, 36, 55-66.
66. Diver, S.T.; Giessert, A.J. Enyne metathesis (Enyne bond reorganization). Chem. Rev. 2004, 104, 1317-1382.
67. Trost, B.M.; Trost, M.K. Intramolecular enyne metathesis reaction. Route to bridged bicycles with bridgehead olefins. J. Am. Chem. Soc. 1991, 113, 1850-1852.
68. Trost, B.M.; Hashmi, A.S.K. A cycloaddition approach to cyclopentenes via metalladienes as 4.pi. partners. J. Am. Chem. Soc. 1994, 116, 2183-2184.
69. Mori, M.; Kitamura, T. Ene-yne and alkyne metathesis. In: Comprehensive Organometallic Chemistry III, Transition Metal Organometallics in Organic Synthesis; Hiyama, T., Ed.; Elsevier: London, UK, 2005; pp. 271-310.
70. Mori, M. Enyne metathesis. In: Handbook of Metathesis; Grubbs, R.H., Ed.; WILEY-VCH: Weinheim, Germany, 2003; Vol. 2, pp. 176-204.
71. For selected reviews on alkene ring-closing metathesis (RCM), see: (a) Monfette, S.; Fogg, D.E. Equilibrium ring-closing metathesis. Chem. Rev. 2009, 109, 3783-3816.
72. Monfette, S.; Fogg, D.E. Ring-closing metathesis synthesis of medium and large rings: Challenges and implications for sustainable synthesis. In: Green Metathesis Chemistry - Great Challenges in Synthesis, Catalysis and Nanotechnology. NATO Science for Peace and Security Series - A: Chemistry and Biology Series; Dragutan, V.; Demonceau, A.; Dragutan, I.; Finkelshtein, E.Sh., Eds.; Springer: Dordrecht, 2010; pp. 129-156.
73. Rainer, J.D. Synthesis of natural products containing mediumsize oxygen heterocycles by ring-closing metathesis. In: Metathesis in Natural Product Synthesis: Strategies, Substrates and Catalysts; Cossy, J; Arseniyadis S.; Meyer C., Eds; Wiley-VCH: Weinheim, 2010, pp. 87-127.
74. Van der Broek S.A.M.W.; Meeuwissen, S.A.; Van Delft, F.L.; Rutjes, F.P.J. Natural products containing medium-sized nitrogen heterocycles synthesized by ring-closing alkene metathesis. In: Metathesis in Natural Product Synthesis: Strategies, Substrates and Catalysts; Cossy, J; Arseniyadis S.; Meyer C., Eds; Wiley-VCH: Weinheim, 2010, pp. 45-85.
75. Gaich, T.; Mulzer, J. Recent applications of olefin ring-closing metathesis (RCM) in the synthesis of biologically important alkaloids, terpenoids, polyketides and other secondary metabolites. Curr. Top. Med. Chem. 2005, 5, 1473-1494.
76. Han, S.-Y.; Chang, S. General ring-closing metathesis. In: Handbook of Metathesis; Grubbs, R.H., Ed.; WILEY-VCH: Weinheim, Germany, 2003; Vol. 2, pp. 5-127.
77. For selected reviews on alkene cross-metathesis (CM), see: Prunet, J.; Grimaud L. Cross-metathesis in natural product synthesis. In: Metathesis in Natural Product Synthesis: Strategies, Substrates and Catalysts; Cossy, J; Arseniyadis S.; Meyer C., Eds; Wiley-VCH: Weinheim, 2010, pp. 287-312.
78. Chatterjee, A.K. Olefin cross-metathesis. In: Handbook of Metathesis; Grubbs, R.H., Ed.; WILEY-VCH: Weinheim, Germany, 2003; Vol. 2, pp. 246-292.
79. Katz, T.J.; Sivavec, T.M. Metal-catalyzed rearrangement of alkenealkynes and the stereochemistry of metallacyclobutene ring opening. J. Am. Chem. Soc. 1985, 107, 737-738.
80. Sivavec, T.M.; Katz, T.J.; Chiang, M.Y.; Yang, G.X.-Q. A metal pentadienyl prepared by reacting a metal carbyne with an enyne. Organometallics 1989, 8, 1620-1625.
81. Katz, T.J.; Yang, G.X.-Q. Reactions of enynes with adsorbed metal-carbenes. Tetrahedron Lett. 1991, 32, 5895-5898.
82. Trost, B.M.; Tanoury, G.J. An unusual mechanism of a palladiumcatalyzed intramolecular carbametalation. A novel palladium-catalyzed rearrangement. J. Am. Chem. Soc. 1988, 110, 1636-1638.
83. Trost, B.M.; Trost, M.K. Mechanistic dichotomies in Pd-catalyzed enyne metathesis of cyclic olefins. Tetrahedron Lett. 1991, 32, 3647-3650.
84. Trost, B.M.; Yanai, M.; Hoogsteen, K. A palladium-catalyzed [2 + 2] cycloaddition. Mechanism of a Pd-catalyzed enyne metathesis. J. Am. Chem. Soc. 1993, 115, 5294-5295.
85. Trost, B.M.; Chang, V.K. An Approach to Botrydianes: On the steric demands of a metal catalyzed enyne metathesis. Synthesis 1993, 824-832.
86. 2-catalyzed conversion of 1,6-and 1,7-enynes to 1-vinylcycloalkenes. Anomalous bond connection in skeletal reorganization of enynes. Organometallics, 1996, 15, 901-903.
87. Schrock, R.R.; Hoveyda, A.H. Molybdenum and tungsten imido alkylidene complexes as efficient olefin-metathesis catalysts. Angew. Chem. Int. Ed. 2003, 42, 4592-4633.
88. Singh, R.; Schrock, R.R.; Müller, P.; Hoveyda, A.H. Synthesis of monoalkoxide monopyrrolyl complexes Mo(NR)(CHR′)(OR″)(pyrrolyl): Enyne metathesis with high oxidation state catalysts. J. Am. Chem. Soc. 2007, 129, 12654-12655.
89. Vougioukalakis, G.C.; Grubbs, R.H. Ruthenium-based heterocyclic carbene-coordinated olefin metathesis catalysts. Chem. Rev. 2010, 110, 1746-1787.
90. Trnka T.M.; Grubbs R.H. The development of L2X2Ru=CHR olefin metathesis catalysts: An organometallic success story. Acc. Chem. Res. 2001, 34, 18-29.
91. Dragutan, V.; Dragutan, I.; Delaude, L.; Demonceau, A. NHC-Ru complexes - Friendly catalytic tools for manifold chemical transformations. Coord. Chem. Rev. 2007, 251, 765-794.
92. Monfette, S.; Conrad, J.C.; Blacquiere, J.M.; Beach, N; Fogg, D.E. Ru-Aryloxide catalysts for olefin metathesis. In: Metathesis Chemistry: Nanostructure Design to Advanced Materials.; Imamoglu, Y.; Dragutan, V. Eds.; Springer: Dordrecht, 2007, pp. 79-89.
93. Delaude, L.; Demonceau, A.; Noels, A.F. Synthesis and application of new N-heterocyclic carbene ruthenium complexes in catalysis: A case study. Curr. Org. Chem. 2006, 10, 203-215.
94. Dragutan, V.; Dragutan, I. Ruthenium vinylidene complexes. Syntheses and applications in metathesis catalysis. Platinum Metals Rev. 2004, 48, 148-153.
95. Dragutan, V.; Dragutan, I.; Verpoort, F. Ruthenium indenylidene complexes. Metathesis catalysts with enhanced activity. Platinum Metals Rev. 2005, 49, 33-40.
96. Dragutan, V.; Dragutan, I.; Drozdzak, R.; Verpoort, F. Synthetic approach to ruthenium vinylidene complexes and their applications in metathesis catalysis. Rev. Roum. Chim. 2007, 52, 931-939.
97. Schrodi, Y.; Pederson, R.L. Evolution and applications of second-generation ruthenium olefin metathesis catalysts. Aldrichimica Acta 2007, 40, 45-52.
98. Dragutan, I.; Dragutan, V. Practical new strategies for immobilising ruthenium carbene complexes-Part I. Immobilisation via phosphane, alkylidene and N-heterocyclic carbene ligands. Platinum Metals Rev. 2008, 52, 71-82.
99. Dragutan, I.; Dragutan, V. Practical new strategies for immobilising ruthenium carbene complexes-Part II. Immobilisation via Schiff bases, arenes, and anionic and tagged ligands. Platinum Metals Rev. 2008, 52, 157-162.
100. Samojlowicz, C.; Grela, K. Ruthenium-based olefin metathesis catalysts bearing N-heterocyclic carbene ligands. Chem. Rev. 2009, 109, 3708-3742.
101. Weskamp, T.; Schattenmann, W.C.; Spiegler, M.; Herrmann, W.A. A novel class of ruthenium catalysts for olefin metathesis. Angew. Chem. Int. Ed. 1998, 37, 2490-2493.
102. Huang, J.; Stevens, E.D.; Nolan, S.P.; Peterson, J.L. Olefin metathesis-active ruthenium complexes bearing a nucleophilic carbene ligand. J. Am. Chem. Soc. 1999, 121, 2674-2678.
103. Scholl, M.; Ding, S.; Lee, C.W.; Grubbs, R.H. Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands. Org. Lett. 1999, 1, 953-956.
104. Ding, F.; Sun, Y.; Monsaert, S.; Drozdzak, R.; Dragutan, I.; Dragutan, V.; Verpoort, F. Ruthenium complexes containing bidentate Schiff base ligands as precursors of homogeneous and immobilized catalysts. Curr. Org. Synth., 2008, 5, 291-304.
105. Dragutan, I., Dragutan, V., Filip P. Recent developments in design and synthesis of well-defined ruthenium metathesis catalysts - a highly successful opening for intricate organic synthesis. Arkivoc 2005, X, 105-129.
106. Scholl, M.; Trnka, T.M.; Morgan, J.P.; Grubbs, R.H. Increased ring closing metathesis activity of ruthenium-based olefin metathesis catalysts coordinated with imidazolin-2-ylidene ligands. Tetrahedron Lett. 1999, 40, 2247-2250.
107. Bieniek, M.; Bujok, R.; Cabaj, M.; Lugan, N.; Lavigne, G.; Arlt, D.; Grela, K. Advanced fine-tuning of Grubbs/Hoveyda olefin metathesis catalysts: A further step toward an optimum balance between antinomic properties. J. Am. Chem. Soc. 2006, 128, 13652-13653.
108. Wakamatsu, H.; Blechert, S. A new highly efficient ruthenium metathesis catalyst. Angew. Chem., Int. Ed. 2002, 41, 2403-2405.
109. Zaja, M.; Connon, S.J.; Dunne, A.M.; Rivard, M.; Buschmann, N.; Jiricek, J.; Blechert, S. Ruthenium olefin metathesis catalysts with modified styrene ethers: Influence of steric and electronic effects. Tetrahedron 2003, 59, 6545-6558.
110. 2. J. Am. Chem. Soc. 1994, 116, 6049-6050.
111. Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. Construction of novel polycyclic ring systems by transition-metal-catalyzed cycloisomerization of eneeneynes. Interception of a carbenoid intermediate in skeletal reorganization of enynes. J. Am. Chem. Soc. 1998, 120, 9104-9105.
112. Fürstner, A.; Stelzer, F.; Szillat, H. Platinum-catalyzed cycloisomerization reactions of enynes. J. Am. Chem. Soc. 2001, 123, 11863-11869.
113. Ota, K.; Lee, S.I.; Tang, J.-M.; Takachi, M.; Nakai, H.; Morimoto, T.; Sakurai, H.; Kataoka, K.; Chatani, N. Rh(II)-catalyzed skeletal reorganization of 1,6-and 1,7-enynes through electrophilic activation of alkynes. J. Am. Chem. Soc. 2009, 131, 15203-15211.
114. Ota, K.; Chatani, N. Rh(II)-catalyzed skeletal reorganization of enynes involving selective cleavage of C-C triple bonds. Chem. Commun. 2008, 2906-2907.
115. Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. Skeletal reorganization of enynes to 1-vinylcycloalkenes catalyzed by GaCl3. J. Am. Chem. Soc. 2002, 124, 10294-10295.
116. Watanuki, S.; Ochifuji, N.; Mori, M. Chromium-catalyzed intramolecular enyne metathesis. Organometallics 1994, 13, 4129-4130.
117. Watanuki, S.; Ochifuji, N.; Mori, M. Chromium-catalyzed intramolecular enyne metathesis. Organometallics 1995, 14, 5062-5067.
118. Mori, M. Enyne metathesis. In: Handbook of Metathesis; Grubbs, R.H., Ed.; WILEY-VCH: Weinheim, Germany, 2003; Vol. 2, pp. 176-204.
119. Mori M. Recent progress on enyne metathesis: Its application to syntheses of natural products and related compounds. Materials 2010, 3, 2087-2140.
120. Lippstreu, J.J.; Straub, B.F. Mechanism of enyne metathesis catalyzed by Grubbs ruthenium-carbene complexes: A DFT study. J. Am. Chem. Soc. 2005, 127, 7444-7457.
121. Lloyd-Jones, G.C.; Margue, R.G.; de Vries, J.G. Rate enhancement by ethylene in the Ru-catalyzed ring-closing metathesis of enynes: Evidence for an "ene-then-yne" pathway that diverts through a second catalytic cycle. Angew. Chem. Int. Ed. 2005, 44, 7442-7447.
122. Zhao, Y.; Hoveyda, A.H.; Schrock, R.R. Endo-selective enyne ring-closing metathesis promoted by stereogenic-at-W mono-pyrrolide complexes. Org. Lett. 2011, 13, 784-787.
123. Fischmeister, C.; Bruneau, Ch. Ene-yne cross-metathesis with ruthenium carbene catalysts Beilstein J. Org. Chem. 2011, 7, 156-166.
124. Lee, H.-Y.; Kim, B.G.; Snapper, M.L. A stereoselective enyne cross metathesis. Org. Lett. 2003, 5, 1855-1858.
125. Tonogakia, K.; Mori, M. An improved 1,3-diene synthesis from alkyne and ethylene using cross-enyne metathesis Tetrahedron Lett. 2002, 43, 2235-2238.
126. Trost, B.M.; Hashmi, A.S.K. A Cycloaddition approach to cyclopentenes via metalladienes as 4.pi. partners. J. Am. Chem. Soc. 1994, 116, 2183-2184.
127. Trost, B.M.; Hashmi, A.S.K. On the mechanism of the TCPCHFBcatalyzed metathesis of 1,6-enyne: Evidence for alkylidenepalladium intermediates. Angew. Chem. Int. Ed. 1993, 32, 1085-1087.
128. Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. Construction of novel polycyclic ring systems by transition-metal-catalyzed cycloisomerization of eneeneynes. Interception of a carbenoid intermediate in skeletal reorganization of enynes. J. Am. Chem. Soc. 1998, 120, 9104-9105.
129. Mori, M.; Watanuki, S. New synthesis of pyrrolidine derivatives via the chromacyclobutanes generated from enynes and Fischer carbene complexes. J. Chem. Soc., Chem. Commun. 1992, 1082-1084.
130. Kinoshita, A.; Mori, M. Total synthesis of (-)-stemoamide using rutheniumcatalyzed enyne metathesis reaction. J. Org. Chem. 1996, 61, 8356-8357.
131. Wood, S.A.; Rasmussen, J.P.; Holland, P.T.; Campbell, R.; Crowe, A.L.M. First report of the cyanotoxin anatoxin-a from Aphanizomenon issatschenkoi (cyanobacteria). J. Phycology 2007, 43, 356-365.
132. Brenneman, J.B.; Martin, S.F. Application of intramolecular enyne metathesis to the synthesis of aza[4.2.1]bicyclics: Enantiospecific total synthesis of (+)-anatoxin-a. Org. Lett. 2004, 6, 1329-1331.
133. Brenneman, J.B.; Machauer, R.; Martin, S.F. Enantioselective synthesis of (+)-anatoxin-a via enyne metathesis. Tetrahedron 2004, 60, 7301-7314.
134. Mori, M.; Tomita, T.; Kita, Y.; Kitamura, T. Synthesis of (+)-anatoxin-a using enyne metathesis. Tetrahedron Lett. 2004, 45, 4397-4399.
135. Tomita, T.; Kita, Y.; Kitamura, T.; Sato, Y.; Mori, M. Synthesis of (+)-anatoxin-a using enyne metathesis. Tetrahedron 2006, 62, 10518-10527.
136. Barrett, A.G.M.; Baugh, S.P.D.; Braddock, D.C.; Flack, K.; Gibson, V.C.; Giles, M.R.; Marshall, E.L.; Procopiou, P.A.; White, A.J.P.; Williams, D.J. Rapid entry into mono-, bi-, and tricyclic l-lactam arrays via alkene metathesis. J. Org. Chem. 1998, 63, 7893-7907.
137. Duboc R.; Henaut Ch.; Savignac, M.; Genet J.-P.; Bhatnagar N. Synthetic approach to tricyclic l-lactams using metathesis and Diels-Alder reactions. Tetrahedron Lett. 2001, 42, 2461-2464.
138. Boyer, F.-D.; Hanna, I. Synthesis of allocolchicines using sequential ringclosing enyne metathesis-Diels-Alder reactions. Org. Lett. 2007, 9, 715-718.
139. Hoye, T.R.; Donaldson, S.M.; Vos, T.J. An enyne metathesis/(4 + 2)-dimerization route to (±)-differolide. Org. Lett. 1999, 1, 277-279.
140. Kaliappan, K.P.; Gowrisankar, P. An expedient enyne metathesis approach to dysidiolide. Tetrahedron Lett. 2004, 45, 8207-8209.
141. Isaka, M.; Srisanoh, U.; Veeranondha, S.; Choowong, W.; Lumyong, S. Cytotoxic eremophilane sesquiterpenoids from the saprobic fungus Berkleasmium nigroapicale BCC 8220. Tetrahedron 2009, 65, 8808-8815.
142. Reddy, D.S.; Kozmin, S.A. Efficient and general approach to eremophilanes using siloxyalkyne-alkene metathesis. J. Org. Chem. 2004, 69, 4860-4862.
143. Schramm, M.P.; Reddy, D. S.; Kozmin, S.A. Siloxyalkyne-alkene metathesis: Rapid access to highly functionalized enones. Angew. Chem. Int. Ed. 2001, 40, 4274-4277.
144. Dragutan, V.; Dragutan, I.; Fischer, H. Synthesis of metal-containing polymers via ring opening metathesis polymerization (ROMP). Part I. Polymers containing main group metals, J. Inorg. Organomet. Polym. Mater. 2008, 18, 18-31.
145. Dragutan, I.; Dragutan, V.; Fischer, H. Synthesis of metal-containing polymers via ring opening metathesis polymerization (ROMP). Part II: Polymers containing transition metals. J. Inorg. Organomet. Polym. Mater. 2008, 18, 311-324.
146. Hessler, F.; Cisarova, I.; Sedlak, D.; Bartunek, P.; Kotora, M. Synthesis of ferrocenestrone: the first metallocene based steroid analogue. Chem. Eur. J. 2012, 18, 5515-5518.
147. Aggarwal, V.K.; Astle, C.J.; Roger-Evans, M. A concise asymmetric route to the bridged bicyclic tropane alkaloid ferruginine using enyne ring-closing metathesis. Org. Lett. 2004, 6, 1469-1471.
148. Cheng, G.; Wang, X.; Zhu, R.; Shao, C.; Xu, J.; Hu, Y. Total synthesis of (-)-cocaine and (-)-ferruginine. J. Org. Chem. 2011, 76, 2694-2700.
149. Satcharoen, V.; McLean, N.J.; Kemp, S.C.; Camp, N.P.; Brown, R.C.D. Stereocontrolled synthesis of (-)-galanthamine. Org. Lett. 2007, 9, 1867-1869.
150. Kikuchi, D.; Yoshida, M.; Shishido, K. Total synthesis of (±)-3-hydroxy-l-ionone through a ring-closing enyne metathesis. Synlett 2012, 577-580.
151. Hoye R.T.; Zhao, H. Some allylic substituent effects in ring-closing metathesis reactions: Allylic alcohol activation. Org. Lett. 1999, 1, 1123-1125.
152. Clark, D.A.; Clark, J.R.; Diver, S.T. Alkenol-alkyne cross metathesis. Org. Lett. 2008, 10, 2055-2058.
153. Imahori, T.; Ojima, H.; Yoshimura, Y.; Takahata, H. Acceleration effect of an allylic hydroxy group on ring-closing enyne metathesis of terminal alkynes: Scope, application, and mechanistic insights. Chem. Eur. J. 2008, 14, 10762-10771.
154. Schmidt, B.; Nave, S. Control of ring size selectivity by substrate directable RCM. Chem. Commun. 2006, 2489-2491.
155. Schmidt, B.; Nave, S. Synthesis of dihydrofurans and dihydropyrans with unsaturated side chains based on ring size-selective ring-closing metathesis. Adv. Synth. Catal. 2007, 349, 215-230.
156. Lopez, O.; Bols, M. Isofagomine, noeuromycin and other 1-azasugars, iminosugar-related glycosidase inhibitors. In: Iminosugars: From Synthesis to Therapeutic Applications; Compain, P.; Martin, O.R., Eds.; Wiley-VCH: Weinheim, Germany, 2007; Ch. 6.
157. Takahata, H.; Taguchi, T.; Imahori, T.; Yoshimura, Y.; Kato, A.; Adachi, I.; Kawahata, M.; Yamaguchi, K. Asymmetric synthesis of 2-propylisofagomine using allylic hydroxy group accelerated ring-closing enyne metathesis. Heterocycles 2012, 84, 929-944.
158. Clark, J.S.; Townsend, R.J.; Blake, A.J.; Teat, S.J.; Johns, A. A concise enantioselective synthesis of the AB ring system of the manzamine alkaloids by ring-closing enyne metathesis. Tetrahedron Lett. 2001, 42, 3235-3238.
159. Bedel, O.; Francais, A.; Haudrechy, A. Diastereoselective access to the spirotetronate subunit of the quartromicins. Synlett, 2005, 2313-2316.
160. Kinoshita, A.; Mori, M. Total synthesis of (-)-stemoamide using rutheniumcatalyzed enyne metathesis reaction. Heterocycles 1997, 46, 287-299.
161. Vanga, D.G.; Kaliappan, K.P. Total synthesis and stereochemical assignment of (-)-zenkequinone B. Synlett 2012, 23, 2931-2934.
162. Vougioukalakis, G.C. Removing ruthenium residues from olefin metathesis reaction products. Chem. Eur. J. 2012, 18, 8868-8880.
163. Mori, M.; Sakakibara, N.; Kinoshita, A. Remarkable effect of ethylene gas in the intramolecular enyne metathesis of terminal alkynes. J. Org. Chem. 1998, 63, 6082-6083.
164. Grotevendt, A.G.D.; Lummiss, J.A.M.; Mastronardi, M.L.; Fogg, D.E. Ethylene-promoted vs. ethylene-free enyne metathesis. J. Am. Chem. Soc. 2011, 133, 15918-15921.
165. Kaliappan, K.P.; Ravikumar, V. Angucyclinone antibiotics: Total syntheses of YM-181741, (+)-ochromycinone, (+)-rubiginone B2, (-)-tetrangomycin, and MM-47755. J. Org. Chem. 2007, 72, 6116-6126.
166. Kaliappan, K.P.; Ravikumar, V. First enantioselective total synthesis of the angucyclinone-type antibiotic YM-181741. Synlett 2007, 977-979.
167. Li, J.; Todaro, L.J.; Mootoo, D.R. Synthesis of the AB subunit of angelmicin B through a tandem alkoxy radical fragmentation-etherification sequence. Org. Lett. 2008, 10, 1337-1340.
168. Hu, F.; Zhang Y.-H.; Yao, Z.-J. Parallel synthesis of individual shikimic acid-like molecules using a mixture-operation strategy and ring-closing enyne metathesis. Tetrahedron Lett. 2007, 48, 3511-3515.
169. Krishna, P.R.; Reddy, P.S. Stereoselective total synthesis of (+)-valienamine and (+)-4-epi-valienamine via a ring-closing enyne metathesis protocol. Synlett, 2009, 209-212.
170. Cumpstey, I.; Gehrke, S.; Erfan S.; Cribiu R. Studies on the synthesis of valienamine and 1-epi-valienamine starting from D-glucose or L-sorbose. Carbohydr. Res. 2008, 343, 1675-1692.
171. Trost, B.M.; Chang V.K. An approach to botrydianes: On the steric demands of a metal catalyzed enyne metathesis. Synthesis 1993, 824-832.
172. Padwa, A.; Austin, D.J.; Gareau, Y.; Kassir, J.M.; Xu, S.L. Rearrangement of alkynyl and vinyl carbenoids via the rhodium(II)-catalyzed cyclization reaction of alpha-diazo ketones. J. Am. Chem. Soc. 1993, 115, 2637-2647.
173. Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. Platinum-and acid-catalyzed enyne metathesis reactions: Mechanistic studies and applications to the syntheses of streptorubin B and metacycloprodigiosin. J. Am. Chem. Soc. 1998, 120, 8305-8314.
174. Trost, B.M.; Doherty, G.A. An asymmetric synthesis of the tricyclic core and a formal total synthesis of roseophilin via an enyne metathesis. J. Am. Chem. Soc. 2000, 122, 3801-3810.
175. Kim, S.-H.; Bowden, N.; Grubbs, R.H. Catalytic ring closing metathesis of dienynes: Construction of fused bicyclic rings. J. Am. Chem. Soc. 1994, 116, 10801-10802.
176. Kim, S.-H.; Zuercher, W.J.; Bowden, N.; Grubbs, R.H. Catalytic ring closing metathesis of dienynes: Construction of fused bicyclic [n.m.0] rings. J. Org. Chem. 1996, 61, 1073-1081.
177. Li, J.; Lee, D. Enyne-metathesis-based tandem processes. Eur. J. Org. Chem. 2011, 4269-4287.
178. Porta, M.; Blechert, S. Cascade metathesis in natural product synthesis. In: Metathesis in Natural Product Synthesis: Strategies, Substrates and Catalysts; Cossy, J; Arseniyadis, S.; Meyer, C. Eds.; Wiley-VCH: Weinheim, Germany, 2010; pp. 313-341.
179. Oguri, H.; Yamagishi, Y.; Hiruma, T.; Oikawa, H. Skeletal and stereochemical diversification of tricyclic frameworks inspired by Ca2+-ATPase inhibitors, artemisinin and transtaganolide D. Org. Lett. 2009, 11, 601-604.
180. Boyer, F.D.; Hanna, I. Synthesis of the tricyclic core of colchicine via a dienyne tandem ring-closing metathesis reaction. Org. Lett. 2007, 9, 2293-2295.
181. Srikrishna, A.; Pardeshi, V.H.; Satyanarayana, G. Enantioselective formal total syntheses of clavukerin A and isoclavukerin A via a ring-closing metathesis reaction. Tetrahedron: Asymmetry, 2010, 21, 746-750.
182. Knüppel, S.; Rogachev, V.O.; Metz, P.A. Concise catalytic route to the marine sesquiterpenoids (-)-clavukerin A and (-)-isoclavukerin A. Eur. J. Org. Chem. 2010, 6145-6148.
183. Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Total synthesis of (±)-erythravine based on ring closing dienyne metathesis. Tetrahedron Lett. 2003, 44, 8047-8049.
184. Shimizu, K.; Takimoto, M.; Sato, Y.; Mori, M. Total synthesis of (±)-erythrocarine using dienyne metathesis. J. Organomet. Chem. 2006, 691, 5466-5475.
185. Shimizu, K.; Takimoto, M.; Mori, M. Novel synthesis of heterocycles having a functionalized carbon center via nickel-mediated carboxylation: Total synthesis of erythrocarine. Org. Lett. 2003, 5, 2323-2325.
186. Fukumoto, H.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. Total synthesis of (+)-l-erythroidine. Angew. Chem. Int. Ed. 2006, 45, 2731-2734.
187. Boyer F.-D.; Hanna, I. Synthesis of highly functionalized tricyclic ring systems related to guanacastepene via tandem ring-closing metathesis reaction. Tetrahedron Lett. 2002, 43, 7469-7472
188. Boyer, F.-D.; Hanna, I.; Ri card, L. Formal synthesis of (±)-guanacastepene A: A tandem ring-closing metathesis approach. Org. Lett. 2004, 6, 1817-1820.
189. Krishna, P.R.; Narsingam, M. Studies directed towards the stereoselective total synthesis of ilexlactone via a tandem ring-closing enyne metathesis protocol. Tetrahedron Lett. 2007, 48, 8721-8724.
190. Schubert M.; Metz, P. Enantioselective total synthesis of the diterpenes kempene-2, kempene-1, and 3-epi-kempene-1 from the defense secretion of higher termites. Angew. Chem. Int. Ed. 2011, 50, 2954-2956.
191. Zou, J.; Cho, D.W.; Mariano, P.S. A concise, metathesis based approach to construction of the lepadiformine/cylindricine tricyclic framework. Tetrahedron 2010, 66, 5955-5961.
192. Niethe A.; Fischer D.; Blechert S. Total synthesis of ent-lepadin F and G by a tandem ene-yne-ene ring closing metathesis. J. Org. Chem. 2008, 73, 3088-3093.
193. Collins, S. K.; El-Azizi, Y.; Schmitzer, A. Development of perfluoroarenearene interactions for macrocyclic enyne metathesis and the total synthesis of macrocyclic natural products. J. Org. Chem. 2007, 72, 6397-6408.
194. Layton, M.E.; Morales, C.A.; Shair, M.D. Biomimetic synthesis of (-)-longithorone A. J. Am. Chem. Soc. 2002, 124, 773-775.
195. Ramharter, J.; Weinstabl, H.; Mulzer, J. Synthesis of the lycopodium alkaloid (+)-lycoflexine. J. Am. Chem. Soc. 2010, 132, 14338-14339.
196. Chang, L.; Jiang, H.; Fu, J.; Liu, B.; Li, Ch.-Ch.; Yang, Zh. Synthesizing the tetracyclic core of nanolobatolide. J. Org. Chem. 2012, 77, 3609-3614.
197. Codesido, E.M.; Castedo, L.; Granja, J.R. Access to [6.4.0]carbocyclic systems by tandem metathesis of dienynes. A step toward the synthesis of a PreD3-D3 transition state analogue. Org.Lett. 2001, 3, 1483-1486.
198. Honda, T.; Namiki, H.; Kaneda, K.; Mizutani, H. First diastereoselective chiral synthesis of (-)-securinine. Org. Lett. 2004, 6, 87-89.
199. Honda, T.; Namiki, H.; Watanabe, M.; Mizutani, H. First total synthesis of (+)-viroallosecurinine.Tetrahedron Lett. 2004, 45, 5211-5213.
200. Codesico, E.M.; Castedo, L.; Granja, J.R. Access to [6.4.0]carbocyclic systems by tandem metathesis of dienynes. A step toward the synthesis of a PreD3lD3 transition state analogue. Org. Lett. 2001, 3, 1483-1486.
201. Codesico, E.M.; Rodriguez, J.R.; Castedo, L.; Granja, J.R. Toward an analogue of the transition state of PreD3lD3 isomerization: Stereoselective synthesis of linearly fused 6-8-6 carbocyclic Systems. Org. Lett. 2002, 4, 1651-1654.
202. García-Fandiño, R.; Codesico, E.M.; Sobarzo-Sánchez, E.; Castedo, L.; Granja, J.R. Tandem RCM of dienynes for the construction of taxoltype carbocyclic systems. Org. Lett. 2004, 6, 193-196.
203. Aldengunde, M.J.; García-Fandiño, R.; Castedo, L.; Granja, J.R. Dienyne ring-closing metathesis approach for the construction of taxosteroids. Chem. Eur. J. 2007, 13, 5135-5150.
204. García-Fandiño, R.; Aldengunde, M.J.; Codesico, E.M.; Castedo, L.; Granja, J.R. RCM for the construction of novel steroid-like polycyclic systems. 1. Studies on the synthesis of a PreD3-D3 transition state analogue. J. Org. Chem. 2005, 70, 8281-8290.
205. Aldengunde, M.J.; Castedo, L.; Granja, J.R. Toward an efficient synthesis of taxane analogs by dienyne ring-closing metathesis. Org. Lett. 2008, 10, 3789-3792.
206. Kaliappan, K.P.; Nandurdikar, R.S. A facile domino metathesis route to thapsigargin skeleton. Org. Biomol. Chem. 2005, 3, 3613-3614.
207. Kinoshita, A.; Sakakibara, N.; Mori, M. Novel 1,3-diene synthesis from alkyne and ethylene by ruthenium-catalyzed enyne metathesis. J. Am. Chem. Soc. 1997, 119, 12388-12389.
208. Kinoshita, A.; Sakakibara, N.; Mori, M. Novel 1,3-diene synthesis from alkyne and ethylene by ruthenium-catalyzed enyne metathesis. Tetrahedron 1999, 55, 8155-8167.
209. Mori, M.; Tonogaki, K.; Kinoshita, A. Synthesis of 1,3-diene from alkyne and ethylene: Acetic acid 2-methylene-3-phenethyl-but-3-enyl ester. Org. Synth. 2004, 81, 1-13.
210. Tonogaki, K.; Mori, M. An improved 1,3-diene synthesis from alkyne and ethylene using cross-enyne metathesis. Tetrahedron Lett. 2002, 43, 2235-2238.
211. Stragies, R.; Schuster, M.; Blechert, S. A crossed yne-ene metathesis showing atom economy. Angew. Chem. Int. Ed. 1997, 36, 2518-2520.
212. 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.
213. Schürer, S.C.; Blechert, S. A versatile synthesis of substituted tetrahydropyridines. Tetrahedron Lett. 1999, 40, 1877-1880.
214. Smulik, J.A; Diver, S.T. Terminal alkyne-ethylene cross-metathesis: Reaction of 1-substituted propargyl esters at elevated ethylene pressure. J. Org. Chem. 2000, 65, 1788-1792.
215. Smulik, J.A.; Diver, S.T. Expanded scope in ethylene-alkyne cross-metathesis: Coordinating heteroatom functionality at the propargylic position. Org. Lett. 2000, 2, 2271-2274.
216. Smulik, J.A.; Giessert, A.J.; Diver S.T. Ethylene metathesis of sulfurcontaining alkynes. Tetrahedron Lett. 2002, 43, 209-211.
217. Kotha, S.; Halder, S.; Brahmachary, E. Synthesis of highly functionalized phenylalanine derivatives via cross-enyne metathesis reactions. Tetrahedron 2002, 58, 9203-9208.
218. Mori, M.; Tonogaki, K.; Nishiguchi, N. Syntheses of anolignans A and B using ruthenium-catalyzed cross-enyne metathesis. J. Org. Chem. 2002, 67, 224-226.
219. Kaliappan, K.P.; Subrahmanyam, A.V. A new versatile strategy for C-aryl glycosides. Org. Lett. 2007, 9, 1121-1124.
220. Ayyagari, B.; Subrahmanyam, V.; Palanichamy, K.; Kaliappan, K.P. Application of an enyne metathesis/Diels-Alder cycloaddition sequence: A new versatile approach to the syntheses of C-aryl glycosides and spiro-C-aryl glycosides. Chem. Eur. J. 2010, 16, 8545-8556.
221. Saito, N.; Masuda, M.; Saito, H.; Takenouchi, K.; Ishizuka, S.; Namekawa, J.; Takimoto-Kamimura, M.; Kittaka, A. Synthesis of 24,24-ethanovitamin D3 lactones using ruthenium-catalyzed intermolecular enyne metathesis: Potent vitamin D receptor antagonists. Synthesis 2005, 2533-2543.
222. Kim, C.H.; An, H.J.; Shin, W.K.; Yu, W.; Woo, S.K.; Jung, S.K.; Lee, E. Stereoselective synthesis of (-)-amphidinolide E. Chem. Asian J. 2008, 3, 1523-1534.
223. 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.
224. Chung, Y.K.; Lee, E. Total synthesis of (-)-amphidinolide K. Angew. Chem. Int. Ed. 2009, 48, 2364-2366.
225. Fürstner, A.; Flügge, S.; Larionov, O.; Takahashi, Y.; Kubota, T.; Kobayashi, J. Total synthesis and biological evaluation of amphidinolide V and analogues. Chem. Eur. J. 2009, 15, 4011-4029.
226. Fürstner, A.; Larionov, O.; Flugge, S. What is amphidinolide V? Report on a likely conquest. Angew. Chem. Int. Ed. 2007, 46, 5545-5548.
227. Fürstner, A.; Kattnig, E.; Kelter, G.; Fiebig, H.-H. Molecular editing and biological evaluation of amphidinolide X and Y. Chem. Eur. J. 2009, 15, 4030-4043.
228. Middleton, M.D.; Peppers, B.P.; Diver, S.T. Studies directed toward the synthesis of the scabrosins:validation of a tandem enyne metathesis approach. Tetrahedron 2006, 62, 10528-10540.
229. Kitamura, T.; Saito, Y.; Mori, M. Synthetic study of (+)-anthramycin using ring-closing enyne metathesis and cross-metathesis. Tetrahedron 2004, 60, 9649-9657.
230. 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.
231. Paquette, L.A.; Lai, K.W. Studies directed toward the total synthesis of lancifodilactone G: An expeditious route to the ABC subunit. Org. Lett. 2008, 10, 2111-2113.
232. Jung, M.E.; Chu, H.V. Preparation of a functionalized tetracyclic intermediate for the synthesis of rhodexin A. Org. Lett. 2008, 10, 3647-3649.
233. Jung, M.E.; Yoo, D. First total synthesis of rhodexin A. Org. Lett. 2011, 13, 2698-2701.
234. Jung, M.E.; Chu, H.V. Synthesis of BCD tricyclic analogues of the novel cardiac glycoside rhodexin A. Tetrahedron Lett. 2011, 52, 4312-4314.
235. 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.
236. Kummer, D.A.; Brenneman, J.B.; Martin, S.F. Application of a domino intramolecular enyne metathesis/cross metathesis reaction to the total synthesis of (+)-8-epi-xanthatin. Org. Lett. 2005, 7, 4621-4623.
237. Evans, M.A.; Morken, J.P. Asymmetric synthesis of (-)-dihydroxanthatin by the stereoselective Oshima-Utimoto reaction. Org. Lett. 2005, 7, 3371-3373.
238. Hoye, T.R.; Joen, J. Metathesis involving a relay and applications in natural product synthesis. In: Metathesis in Natural Product Synthesis; Cossy, J.; Arseniyadis, S.; Meyer, C. Eds. Wiley-VCH: Weinheim, Germany, 2010; Ch. 9, pp. 261-285.
239. El-Azizi, Y.; Zakarian, J.E.; Bouillerand, L.; Schmitzer, A.R.; Collins, S.K. Efficient macrocyclizations via metathesis employing amide-based auxiliaries. Adv. Synth. Catal. 2008, 350, 2219-2225.
240. Collins, S.K.; El-Azizi, Y.; Schmitzer, A. Development of perfluoroarene-arene interactions for macrocyclic enyne metathesis and the total synthesis of macrocyclic natural products. J. Org. Chem. 2007, 72, 6397-6408.
241. Collins, S. K. Preparation of cyclic molecules bearing strained olefins using olefin metathesis. J. Organomet. Chem. 2006, 691, 5122-5128.
242. Zakarian, J.E.; El-Azizi, Y.; Collins, S.K. Exploiting quadrupolar interactions in the synthesis of the macrocyclic portion of longithorone C. Org. Lett. 2008, 10, 2927-2930.
243. Wei, H.; Qiao, C.; Liu, G.; Yang, Z.; Li, C.-C. Stereoselective total syntheses of (-)-flueggine A and (+)-virosaine B. Angew. Chem. Int. Ed. 2013, 52, 620-624.
244. Li, J.; Lee, D. Application of a tandem metathesis to the synthesis of (+)-panepophenanthrin. Chem. Asian J. 2010, 5, 1298-1302.
245. Fu, G.C.; Grubbs, R.H. The application of catalytic ring-closing olefin metathesis to the synthesis of unsaturated oxygen heterocycles. J. Amer. Chem. Soc. 1992, 114, 5426-5427.
246. Chang, S.; Grubbs R.H. A simple method to polyhydroxylated olefinic molecules using ring-closing olefin metathesis. Tetrahedron Lett. 1997, 38, 4757-4760.
247. Kim, Y.J.; Lee, D. Synthesis of the entire framework of tartrolon B utilizing a silicon-tethered ring-closing metathesis strategy. Org. Lett. 2006, 8, 5219-5222.
248. Mukherjee, S.; Lee, D. Application of tandem ring-closing enyne metathesis: Formal total synthesis of (-)-cochleamycin A. Org. Lett. 2009, 11, 2916-2919.
249. Movassaghi, M.; Piizzi, G.; Siegel, D.S.; Piersanti, G. Enantioselective total synthesis of (l)-acylfulvene and (l)-irofulven. Angew. Chem. Int. Ed. 2006, 45(35) 5859-5863.
250. Movassaghi M, Piizzi G, Siegel DS, Piersanti G. Observations in the synthesis of the core of the antitumor illudins via an enyne ring closing metathesis cascade. Tetrahedron Lett. 2009, 50, 5489-5492.
251. Kress, S.; Weckesser, J.; Schulz, S.R.; Blechert, S. Concise total syntheses of dipiperidine alkaloids virgidivarine and virgiboidine through Ru-mediated ene-ene-yne ring rearrangement metathesis (RRM). Eur. J. Org. Chem. 2013, 1346-1355.
252. Li, J.; Park, S.; Miller, R.L.; Lee, D. Tandem enyne metathesis-metallotropic [1,3]-shift for a concise total syntheses of (+)-asperpentyn, (-)-harveynone, and (-)-tricholomenyn A. Org. Lett. 2009, 11, 571-574.
253. Cho, E.J.; Lee, D. Total synthesis of (3R,9R,10R)-panaxytriol via tandem metathesis and metallotropic [1,3]-shift as a key step. Org. Lett. 2008, 10, 257-259.