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Wang, K.K.1
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Reviews of enediyne antibiotics: (a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (b) Maier, M. E. Synlett 1995, 13. (c) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.
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Nicolaou, K.C.1
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85049949910
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Reviews of enediyne antibiotics: (a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (b) Maier, M. E. Synlett 1995, 13. (c) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.
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Maier, M.E.1
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4
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0030005845
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Reviews of enediyne antibiotics: (a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (b) Maier, M. E. Synlett 1995, 13. (c) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.
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Grissom, J.W.1
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Huang, D.4
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5
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0000711103
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Danheiser, R. L.; Gould, A. E.; de la Pradilla, R. F.; Helgason, A. L. J. Org. Chem. 1994, 59, 5514.
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Danheiser, R.L.1
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6
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-
0003992923
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Israel Program for Scientific Translation (Mandel, L. Trans.): Jerusalem
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For the intermolecular cycloaddition of enynes: (a) Onischenko, A. S. Diene Synthesis; Israel Program for Scientific Translation (Mandel, L. Trans.): Jerusalem, 1964; pp 249-254 and 635-637. (b) Johnson, R. P. Chem. Rev. 1989, 89, 1111.
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Diene Synthesis
, pp. 249-254
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Onischenko, A.S.1
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7
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-
33845183891
-
-
For the intermolecular cycloaddition of enynes: (a) Onischenko, A. S. Diene Synthesis; Israel Program for Scientific Translation (Mandel, L. Trans.): Jerusalem, 1964; pp 249-254 and 635-637. (b) Johnson, R. P. Chem. Rev. 1989, 89, 1111.
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Johnson, R.P.1
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33748244108
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(a) Christl, M.; Braun, M.; Müller, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 473.
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Christl, M.1
Braun, M.2
Müller, G.3
-
10
-
-
0013081858
-
-
For reactions of this type that proceed through cationic intermediates, see: (a) Whitlock, H.; Wu, W. E.-M.; Whitlock, B. J. J. Org. Chem. 1969, 34, 1857. (b) Hoffmann, H. M. R.; Krumwiede, D.; Mucha, B.; Oehlerking, H. H.; Prahst, G. W. Tetrahedron 1993, 49, 8999. (c) Miller, B.; Ionescu, D. Tetrahedron Lett. 1994, 35, 6615.
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Whitlock, H.1
Wu, W.E.-M.2
Whitlock, B.J.3
-
11
-
-
0027442601
-
-
For reactions of this type that proceed through cationic intermediates, see: (a) Whitlock, H.; Wu, W. E.-M.; Whitlock, B. J. J. Org. Chem. 1969, 34, 1857. (b) Hoffmann, H. M. R.; Krumwiede, D.; Mucha, B.; Oehlerking, H. H.; Prahst, G. W. Tetrahedron 1993, 49, 8999. (c) Miller, B.; Ionescu, D. Tetrahedron Lett. 1994, 35, 6615.
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(1993)
Tetrahedron
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Hoffmann, H.M.R.1
Krumwiede, D.2
Mucha, B.3
Oehlerking, H.H.4
Prahst, G.W.5
-
12
-
-
0028106708
-
-
For reactions of this type that proceed through cationic intermediates, see: (a) Whitlock, H.; Wu, W. E.-M.; Whitlock, B. J. J. Org. Chem. 1969, 34, 1857. (b) Hoffmann, H. M. R.; Krumwiede, D.; Mucha, B.; Oehlerking, H. H.; Prahst, G. W. Tetrahedron 1993, 49, 8999. (c) Miller, B.; Ionescu, D. Tetrahedron Lett. 1994, 35, 6615.
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, pp. 6615
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Miller, B.1
Ionescu, D.2
-
13
-
-
0029945893
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Burrell, R. C.; Daoust, K. J.; Bradley, A. Z.; DiRico, K. J.; Johnson, R. P. J. Am. Chem. Soc. 1996, 118, 4218.
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-
Burrell, R.C.1
Daoust, K.J.2
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DiRico, K.J.4
Johnson, R.P.5
-
15
-
-
0000509322
-
-
Trost, B. M., Fleming, I. Eds., Pergamon: Oxford, Chapter 2.4
-
Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds., Pergamon: Oxford, 1991; Vol. 3, Chapter 2.4.
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, vol.3
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Sonogashira, K.1
-
16
-
-
33947299087
-
-
(a) Bossenbroek, B.; Sanders, D. C.; Curry, H. M.; Shechter, H. J. Am. Chem. Soc. 1969, 91, 371.
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-
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Bossenbroek, B.1
Sanders, D.C.2
Curry, H.M.3
Shechter, H.4
-
18
-
-
85034483221
-
-
note
-
4 cat., 90°C, acetonitrile or pyrrolidine].
-
-
-
-
19
-
-
85034484581
-
-
Self-coupling of 2 gave variable amounts of regioisomeric butenynes and the diyne as byproducts.
-
(a) Self-coupling of 2 gave variable amounts of regioisomeric butenynes and the diyne as byproducts.
-
-
-
-
20
-
-
85034485543
-
-
2 (80% D) in pyrrolidine-N-d (65% D).
-
2 (80% D) in pyrrolidine-N-d (65% D).
-
-
-
-
23
-
-
85034477990
-
-
note
-
15b However, this process could be considered as a type I Cyclization.
-
-
-
-
25
-
-
85034479387
-
-
note
-
3N (1 equiv), toluene, 23°C, 12 h; 60%, 83% based on unrecovered 1].
-
-
-
-
26
-
-
85034484417
-
-
1H NMR spectra with that of 4
-
1H NMR spectra with that of 4.
-
-
-
-
27
-
-
85034472768
-
-
note
-
11
-
-
-
-
28
-
-
85034487116
-
-
The configuration of enyne 19, isolated as a single isomer, was not determined
-
(c) The configuration of enyne 19, isolated as a single isomer, was not determined.
-
-
-
-
29
-
-
85034479368
-
-
Stang, P. J., Diederich, F. Eds.; VCH: Weinheim, Chapter 8.4
-
(a) Gleiter, R.; Herger, R. In Modern Acetylenic Chemistry; Stang, P. J., Diederich, F. Eds.; VCH: Weinheim, 1995. Chapter 8.4.
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(1995)
Modern Acetylenic Chemistry
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Gleiter, R.1
Herger, R.2
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31
-
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0027378315
-
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Alami, M.; Ferri, F.; Linstrumelle, G. Tetrahedron Lett. 1993, 34, 6403.
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(1993)
Tetrahedron Lett.
, vol.34
, pp. 6403
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Alami, M.1
Ferri, F.2
Linstrumelle, G.3
-
32
-
-
85034463124
-
-
note
-
2O (5 mol %), pyrrolidine, 50°C, 16 h] although the isolated yield was low (8%). See Experimental Section for details.
-
-
-
-
34
-
-
33845282860
-
-
(b) Trost, B. M.; Chan, C.; Rühter, G. J. Am. Chem. Soc. 1987, 109, 3486.
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Trost, B.M.1
Chan, C.2
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-
35
-
-
0024836438
-
-
(c) Trost, B. M.; Matsubara, S.; Caringi, J. J. J. Am. Chem. Soc. 1989, 111, 8745.
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Trost, B.M.1
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Caringi, J.J.3
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36
-
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0000375824
-
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(d) Wagner, R. W.; Johnson, T. E.; Li, F.; Lindsey, J. S. J. Org. Chem. 1995, 60, 5266.
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Wagner, R.W.1
Johnson, T.E.2
Li, F.3
Lindsey, J.S.4
-
37
-
-
0031046817
-
-
(e) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rühter, G. J. Am. Chem. Soc. 1997, 119, 698.
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-
Trost, B.M.1
Sorum, M.T.2
Chan, C.3
Harms, A.E.4
Rühter, G.5
-
39
-
-
0000915488
-
-
The regiochemistry of the insertion is contrary to that observed in the Heck reaction between iodoarenes and disubstituted alkynes similar to those used in this work: Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron 1985, 41, 5121.
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(1985)
Tetrahedron
, vol.41
, pp. 5121
-
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Arcadi, A.1
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Marinelli, F.3
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40
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0026491187
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Feldman, K. S.; Ruckle, R. E.; Ensel, S. M.; Weinreb, P. H. Tetrahedron Lett. 1992, 33, 7101.
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Feldman, K.S.1
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Weinreb, P.H.4
-
41
-
-
2242484079
-
-
Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, Chapter 3.4
-
Farina, V. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 3.4.
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(1995)
Comprehensive Organometallic Chemistry II
, vol.12
-
-
Farina, V.1
-
42
-
-
85034467138
-
-
25b (60% yield)
-
25b (60% yield),
-
-
-
-
43
-
-
0028213040
-
-
(b) Burke, S. D.; Piscopio, A. D.; Kort, M. E.; Matulenko, M. A.; Parker, M. H.; Armistead, D. M.; Shankaran, K. J. J. Org. Chem. 1994, 59, 332.
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Burke, S.D.1
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Kort, M.E.3
Matulenko, M.A.4
Parker, M.H.5
Armistead, D.M.6
Shankaran, K.J.7
-
44
-
-
85034483505
-
-
note
-
2/LiCl (pyridine solutions), which suggests that Cu(I) is the actual catalyst.
-
-
-
-
45
-
-
85034475407
-
-
note
-
Protonation of the alkyne by the pyrrolidinium salts, which are soluble under the reaction conditions, may play a role in the process. Piperidinium iodide is insoluble in neat piperidine at room temperature.
-
-
-
-
46
-
-
0001392827
-
-
For recent lead references on the synthesis of enynes: (a) Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968.
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(1996)
Organometallics
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, pp. 3968
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Yi, C.S.1
Liu, N.2
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47
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0029798564
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(b) Wang, K. K.; Wang, Z.; Tarli, A.; Gannett, P. J. Am. Chem. Soc. 1996, 118, 10783.
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Wang, K.K.1
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48
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0000886111
-
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(c) Yamaguchi, M.; Kido, Y.; Omata, K.; Hirama, M. Synlett 1995, 1181.
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Yamaguchi, M.1
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50
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33947299087
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Bossenbroek, B.; Sanders, D. C.; Curry, H. M.; Shechter, H. J. Am. Chem. Soc. 1969, 91, 371.
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Bossenbroek, B.1
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Curry, H.M.3
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53
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0010891052
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Nelson, J. H.; Verstuyft, A. W.; Kelly, J. D.; Jonassen, H. B. Inorg. Chem. 1974, 13, 27.
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Nelson, J.H.1
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Pipoh, R.; van Eldik, R.; Henkel, G. Organometallics 1993, 12, 2236.
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, pp. 2236
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Pipoh, R.1
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55
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84985569484
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Sugihara, Y.; Yamamoto, H.; Mizoue, K.; Murata, I. Angew. Chem., Int. Ed. Engl. 1987, 26, 1247.
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Angew. Chem., Int. Ed. Engl.
, vol.26
, pp. 1247
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Sugihara, Y.1
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56
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0025945137
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Magriotis, P. A.; Scott, M. E.; Kim, K. D. Tetrahedron Lett. 1991, 32, 6085.
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, pp. 6085
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Magriotis, P.A.1
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57
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0002475053
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Renaldo, A. F.; Labadie, J. W.; Stille, J. K. Org. Synth. 1988, 67, 86.
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Renaldo, A.F.1
Labadie, J.W.2
Stille, J.K.3
-
58
-
-
85034483502
-
-
note
-
The regiochemistry of 4 was determined on the basis of HMQC and HMBC experiments. Its configuration was determined on the basis of NOESY experiments (800 and 400 ms mixing time).
-
-
-
-
59
-
-
0031046817
-
-
2,6-Dimethyl-5-methylidene-3-heptyne-2,6-diol, obtained as a byproduct in some of the couplings of alkyne 2, was prepared according to the published procedure: Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rühter, G. J. Am. Chem. Soc. 1997, 119, 698.
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J. Am. Chem. Soc.
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Trost, B.M.1
Sorum, M.T.2
Chan, C.3
Harms, A.E.4
Rühter, G.5
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