-
1
-
-
0013106233
-
-
For antibiotic uses, see: a, Oxford University Press, Oxford
-
For antibiotic uses, see: a) W. Cabri, R. Di Fabio, From Bench to Market: The Evolution of Chemical Synthesis; Oxford University Press, Oxford, 2000;
-
(2000)
From Bench to Market: The Evolution of Chemical Synthesis
-
-
Cabri, W.1
Di Fabio, R.2
-
2
-
-
0001117281
-
-
Ed, G. Lukacs, Springer, Berlin
-
b) R. Southgate, C. Branch, S. Coulton, E. Hunt in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products (Ed.: G. Lukacs), Springer, Berlin, 1993, vol. 2, p. 621;
-
(1993)
Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products
, vol.2
, pp. 621
-
-
Southgate, R.1
Branch, C.2
Coulton, S.3
Hunt, E.4
-
3
-
-
53849110862
-
-
M. I. Page (Ed.), The Chemistry of β-Lactams, Chapman and Hall, London, 1992.
-
c) M. I. Page (Ed.), The Chemistry of β-Lactams, Chapman and Hall, London, 1992.
-
-
-
-
4
-
-
19944428649
-
-
For nonantibiotic uses, see: d
-
For nonantibiotic uses, see: d) J. D. Rothstein, S. Patel, M. R. Regan, C. Haenggeli, Y. H. Huang, D. E. Bergles, L. Jin, M. D. Hoberg, S. Vidensky, D. S. Chung, S. V. Toan, L. I. Bruijn, Z.-z. Su, P. Gupta, P. B. Fisher, Nature 2005, 433, 73;
-
(2005)
Nature
, vol.433
, pp. 73
-
-
Rothstein, J.D.1
Patel, S.2
Regan, M.R.3
Haenggeli, C.4
Huang, Y.H.5
Bergles, D.E.6
Jin, L.7
Hoberg, M.D.8
Vidensky, S.9
Chung, D.S.10
Toan, S.V.11
Bruijn, L.I.12
Su, Z.-Z.13
Gupta, P.14
Fisher, P.B.15
-
6
-
-
5344243182
-
-
f) L. Kvaerno, T. Ritter, M. Werder, H. Hauser, E. M. Carreira, Angew. Chem. Int. Ed. 2004, 43, 4653;
-
(2004)
Angew. Chem. Int. Ed
, vol.43
, pp. 4653
-
-
Kvaerno, L.1
Ritter, T.2
Werder, M.3
Hauser, H.4
Carreira, E.M.5
-
7
-
-
0042423395
-
-
g) G. Veinberg, M. Vorona, I. Shestakova, I. Kanepe, E. Lukevics, Curr. Med. Chem. 2003, 10, 1741.
-
(2003)
Curr. Med. Chem
, vol.10
, pp. 1741
-
-
Veinberg, G.1
Vorona, M.2
Shestakova, I.3
Kanepe, I.4
Lukevics, E.5
-
8
-
-
36849034419
-
-
For selected reviews, see: a
-
For selected reviews, see: a) B. Alcaide, P. Almendros, C. Aragoncillo, Chem. Rev. 2007, 107, 4437;
-
(2007)
Chem. Rev
, vol.107
, pp. 4437
-
-
Alcaide, B.1
Almendros, P.2
Aragoncillo, C.3
-
10
-
-
3042619331
-
-
c) A. R. A. S. Deshmukh, B. M. Bhawal, D. Krishnaswamy, V. V. Govande, B. A. Shinkre, A. Jayanthi, Curr. Med. Chem. 2004, 11, 1889;
-
(2004)
Curr. Med. Chem
, vol.11
, pp. 1889
-
-
Deshmukh, A.R.A.S.1
Bhawal, B.M.2
Krishnaswamy, D.3
Govande, V.V.4
Shinkre, B.A.5
Jayanthi, A.6
-
12
-
-
0035215545
-
-
e) C. Palomo, J. M. Aizpurua, I. Ganboa, M. Oiarbide, Synlett 2001, 1813;
-
(2001)
Synlett
, pp. 1813
-
-
Palomo, C.1
Aizpurua, J.M.2
Ganboa, I.3
Oiarbide, M.4
-
15
-
-
0033008314
-
-
h) C. Palomo, J. M. Aizpurua, I. Ganboa, M. Oiarbide, Amino-Acids 1999, 16, 321;
-
(1999)
Amino-Acids
, vol.16
, pp. 321
-
-
Palomo, C.1
Aizpurua, J.M.2
Ganboa, I.3
Oiarbide, M.4
-
16
-
-
0001197816
-
-
i) M. S. Manhas, D. R. Wagle, J. Chiang, A. K. Bose, Heterocycles 1988, 27, 1755.
-
(1988)
Heterocycles
, vol.27
, pp. 1755
-
-
Manhas, M.S.1
Wagle, D.R.2
Chiang, J.3
Bose, A.K.4
-
18
-
-
84891029339
-
-
F. Diederich, P. J. Stang, R. R. Tykwinski Eds, Wiley-VCH, Weinheim
-
b) F. Diederich, P. J. Stang, R. R. Tykwinski (Eds.), Acetylene Chemistry: Chemistry, Biology and Materials Science, Wiley-VCH, Weinheim, 2005;
-
(2005)
Acetylene Chemistry: Chemistry, Biology and Materials Science
-
-
-
20
-
-
0034604562
-
-
For reviews, see: a
-
For reviews, see: a) P. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem. Int. Ed. 2000, 39, 2632;
-
(2000)
Angew. Chem. Int. Ed
, vol.39
, pp. 2632
-
-
Siemsen, P.1
Livingston, R.C.2
Diederich, F.3
-
21
-
-
0142175456
-
-
b) D. R. Kanis, M. A. Ratner, T. J. Marks, Chem. Rev. 1994, 94, 195;
-
(1994)
Chem. Rev
, vol.94
, pp. 195
-
-
Kanis, D.R.1
Ratner, M.A.2
Marks, T.J.3
-
28
-
-
34547635484
-
-
For recent selected examples for the homocoupling of alkynes, see: a
-
For recent selected examples for the homocoupling of alkynes, see: a) B. J. Morgan, X. Xie, P.-W. Phuan, M. C. Kozlowski, J. Org. Chem. 2007, 72, 6171;
-
(2007)
J. Org. Chem
, vol.72
, pp. 6171
-
-
Morgan, B.J.1
Xie, X.2
Phuan, P.-W.3
Kozlowski, M.C.4
-
29
-
-
0042338464
-
-
b) S. V. Damle, D. Seomoon, P. H. Lee, J. Org. Chem. 2003, 68, 7085;
-
(2003)
J. Org. Chem
, vol.68
, pp. 7085
-
-
Damle, S.V.1
Seomoon, D.2
Lee, P.H.3
-
30
-
-
0037423986
-
-
c) I. J. S. Fairlamb, P. S. Bäuerelein, L. R. Marrison, J. M. Dickinson, Chem. Commun. 2003, 632;
-
(2003)
Chem. Commun
, pp. 632
-
-
Fairlamb, I.J.S.1
Bäuerelein, P.S.2
Marrison, L.R.3
Dickinson, J.M.4
-
31
-
-
0141627460
-
-
d) Y. Liao, R. Fathi, Z. Yang, Org. Lett. 2003, 5, 909;
-
(2003)
Org. Lett
, vol.5
, pp. 909
-
-
Liao, Y.1
Fathi, R.2
Yang, Z.3
-
32
-
-
19544367620
-
-
e) J.-H. Li, Y. Liang, Y.-X. Xie, J. Org. Chem. 2005, 70, 4393;
-
(2005)
J. Org. Chem
, vol.70
, pp. 4393
-
-
Li, J.-H.1
Liang, Y.2
Xie, Y.-X.3
-
33
-
-
12944321352
-
-
f) J.-H. Li, Y. Liang, X.-D. Zhang, Tetrahedron 2005, 61, 1903;
-
(2005)
Tetrahedron
, vol.61
, pp. 1903
-
-
Li, J.-H.1
Liang, Y.2
Zhang, X.-D.3
-
34
-
-
19944432173
-
-
g) A. S. Batsanov, J. C. Collings, I. J. S. Fairlamb, J. P. Holland, J. A. K. Howard, Z. Lin, T. B. Marder, A. C. Parsons, R. M. Ward, J. Zhu, J. Org. Chem. 2005, 70, 703;
-
(2005)
J. Org. Chem
, vol.70
, pp. 703
-
-
Batsanov, A.S.1
Collings, J.C.2
Fairlamb, I.J.S.3
Holland, J.P.4
Howard, J.A.K.5
Lin, Z.6
Marder, T.B.7
Parsons, A.C.8
Ward, R.M.9
Zhu, J.10
-
35
-
-
33645957688
-
-
h) H.-F. Jiang, J.-Y. Tang, A.-Z. Wang, G.-H. Deng, S.-R. Yang, Synthesis 2006, 1155;
-
(2006)
Synthesis
, pp. 1155
-
-
Jiang, H.-F.1
Tang, J.-Y.2
Wang, A.-Z.3
Deng, G.-H.4
Yang, S.-R.5
-
38
-
-
0037144690
-
-
For recent selected references on heterocoupling alkyne reactions, see: k
-
For recent selected references on heterocoupling alkyne reactions, see: k) J. P. Marino, H. N. Nguyen, J. Org. Chem. 2002, 67, 6841;
-
(2002)
J. Org. Chem
, vol.67
, pp. 6841
-
-
Marino, J.P.1
Nguyen, H.N.2
-
42
-
-
34548654368
-
-
See, for instance: a
-
See, for instance: a) B. Alcaide, P. Almendros, T. Martínez del Campo, Angew. Chem. Int. Ed. 2007, 46, 6684;
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 6684
-
-
Alcaide, B.1
Almendros, P.2
Martínez del Campo, T.3
-
43
-
-
53849128160
-
-
Angew. Chem. 2007, 119, 6804;
-
(2007)
Angew. Chem
, vol.119
, pp. 6804
-
-
-
44
-
-
34547173252
-
-
b) B. Alcaide, P. Almendros, T. Martínez del Campo, R. Rodríguez-Acebes, Adv. Synth. Catal. 2007, 349, 749;
-
(2007)
Adv. Synth. Catal
, vol.349
, pp. 749
-
-
Alcaide, B.1
Almendros, P.2
Martínez del Campo, T.3
Rodríguez-Acebes, R.4
-
45
-
-
33746294191
-
-
c) B. Alcaide, P. Almendros, T. Martínez del Campo, Angew. Chem. Int. Ed. 2006, 45, 4501;
-
(2006)
Angew. Chem. Int. Ed
, vol.45
, pp. 4501
-
-
Alcaide, B.1
Almendros, P.2
Martínez del Campo, T.3
-
46
-
-
34547214986
-
-
Angew. Chem. 2006, 118, 4613;
-
(2006)
Angew. Chem
, vol.118
, pp. 4613
-
-
-
47
-
-
33745492598
-
-
d) B. Alcaide, P. Almendros, A. Luna, M. R. Torres, J. Org. Chem. 2006, 71, 4818;
-
(2006)
J. Org. Chem
, vol.71
, pp. 4818
-
-
Alcaide, B.1
Almendros, P.2
Luna, A.3
Torres, M.R.4
-
48
-
-
33645307693
-
-
e) B. Alcaide, P. Almendros, J. M. Alonso, Chem. Eur. J. 2006, 12, 2874;
-
(2006)
Chem. Eur. J
, vol.12
, pp. 2874
-
-
Alcaide, B.1
Almendros, P.2
Alonso, J.M.3
-
49
-
-
33645064286
-
-
f) B. Alcaide, P. Almendros, R. Rodríguez-Acebes, J. Org. Chem. 2006, 71, 2346;
-
(2006)
J. Org. Chem
, vol.71
, pp. 2346
-
-
Alcaide, B.1
Almendros, P.2
Rodríguez-Acebes, R.3
-
51
-
-
32044451039
-
-
h) B. Alcaide, P. Almendros, C. Aragoncillo, M. C. Redondo, M. R. Torres, Chem. Eur. J. 2006, 12, 1539.
-
(2006)
Chem. Eur. J
, vol.12
, pp. 1539
-
-
Alcaide, B.1
Almendros, P.2
Aragoncillo, C.3
Redondo, M.C.4
Torres, M.R.5
-
52
-
-
17044411712
-
-
a) B. Alcaide, P. Almendros, R. Rodríguez-Acebes, J. Org. Chem. 2005, 70, 2713;
-
(2005)
J. Org. Chem
, vol.70
, pp. 2713
-
-
Alcaide, B.1
Almendros, P.2
Rodríguez-Acebes, R.3
-
53
-
-
0037006835
-
-
b) B. Alcaide, P. Almendros, C. Aragoncillo, Chem. Eur. J. 2002, 8, 1719;
-
(2002)
Chem. Eur. J
, vol.8
, pp. 1719
-
-
Alcaide, B.1
Almendros, P.2
Aragoncillo, C.3
-
54
-
-
0035958460
-
-
c) B. Alcaide, P. Almendros, C. Aragoncillo, R. Rodríguez-Acebes, J. Org. Chem. 2001, 66, 5208.
-
(2001)
J. Org. Chem
, vol.66
, pp. 5208
-
-
Alcaide, B.1
Almendros, P.2
Aragoncillo, C.3
Rodríguez-Acebes, R.4
-
55
-
-
0141427680
-
-
2-Symmetrical compound (+)-2a can be considered as a hybrid scaffold as a combination of the naturally occurring β-lactam and 1,3-diyne moieties. For a review on natural product hybrids, see: a) L. F. Tietze, H. P. Bell, S. Chandrasekhar, Angew. Chem. Int. Ed. 2003, 42, 3996.
-
2-Symmetrical compound (+)-2a can be considered as a hybrid scaffold as a combination of the naturally occurring β-lactam and 1,3-diyne moieties. For a review on natural product hybrids, see: a) L. F. Tietze, H. P. Bell, S. Chandrasekhar, Angew. Chem. Int. Ed. 2003, 42, 3996.
-
-
-
-
56
-
-
33846295181
-
-
2-symmetrical natural products, see: b M. Vrettou, A. A. Gray, A. R. E. Brewer, A. G. M. Barrett, Tetrahedron 2007, 63, 1487.
-
2-symmetrical natural products, see: b) M. Vrettou, A. A. Gray, A. R. E. Brewer, A. G. M. Barrett, Tetrahedron 2007, 63, 1487.
-
-
-
-
57
-
-
53849149316
-
-
In addition to being odorless, K2CO3 can be easily removed by aqueous workup. To the best of our knowledge, this is the first time that K2CO3 has been used for the dimerization of terminal alkynes
-
3 has been used for the dimerization of terminal alkynes.
-
-
-
-
58
-
-
33645499678
-
-
Unsymmetrical diynes play an important structural role in many natural products and possess a wide range of potential applications in material science. For selected natural products references, see: a S. López, F. Fernández-Trillo, P. Midón, L. Castedo, C. Saá, J. Org. Chem. 2006, 71, 2802;
-
Unsymmetrical diynes play an important structural role in many natural products and possess a wide range of potential applications in material science. For selected natural products references, see: a) S. López, F. Fernández-Trillo, P. Midón, L. Castedo, C. Saá, J. Org. Chem. 2006, 71, 2802;
-
-
-
-
59
-
-
33646789860
-
-
b) G. Sabitha, C. S. Reddy, J. S. Yadav, Tetrahedron Lett. 2006, 47, 4513;
-
(2006)
Tetrahedron Lett
, vol.47
, pp. 4513
-
-
Sabitha, G.1
Reddy, C.S.2
Yadav, J.S.3
-
60
-
-
30944458384
-
-
c) B. W. Gung, R. M. Fox, R. Falconer, D. Shissler, Tetrahedron: Asymmetry 2006, 17, 40;
-
(2006)
Tetrahedron: Asymmetry
, vol.17
, pp. 40
-
-
Gung, B.W.1
Fox, R.M.2
Falconer, R.3
Shissler, D.4
-
61
-
-
28744434817
-
-
d) H. Yun, T.-C. Chou, H. Dong, Y. Tian, Y.-M. Li, S. J. Danishefsky, J. Org. Chem. 2005, 70, 10375;
-
(2005)
J. Org. Chem
, vol.70
, pp. 10375
-
-
Yun, H.1
Chou, T.-C.2
Dong, H.3
Tian, Y.4
Li, Y.-M.5
Danishefsky, S.J.6
-
62
-
-
27744578693
-
-
e) D. Alves, C. W. Nogueira, G. Zeni, Tetrahedron Lett. 2005, 46, 8761.
-
(2005)
Tetrahedron Lett
, vol.46
, pp. 8761
-
-
Alves, D.1
Nogueira, C.W.2
Zeni, G.3
-
63
-
-
33745442411
-
-
For selected material science references, see: f
-
For selected material science references, see: f) X. Nie, G. Wang, J. Org. Chem. 2006, 71, 4734;
-
(2006)
J. Org. Chem
, vol.71
, pp. 4734
-
-
Nie, X.1
Wang, G.2
-
64
-
-
33645074395
-
-
g) C. Klinger, O. Vostrowsky, A. Hirsch, Eur. J. Org. Chem. 2006, 6, 1508;
-
(2006)
Eur. J. Org. Chem
, vol.6
, pp. 1508
-
-
Klinger, C.1
Vostrowsky, O.2
Hirsch, A.3
-
65
-
-
33746995964
-
-
h) N. Hayashi, T. Matsukihira, K. Miyabayashi, M. Miyake, H. Higuchi, Tetrahedron Lett. 2006, 47, 5585;
-
(2006)
Tetrahedron Lett
, vol.47
, pp. 5585
-
-
Hayashi, N.1
Matsukihira, T.2
Miyabayashi, K.3
Miyake, M.4
Higuchi, H.5
-
66
-
-
19944417960
-
-
i) S. A. Vail, P. J. Krawczuk, D. M. Guldi, A. Palkar, L. Echegoyen, J. P. Tome, M. A. Fazio, D. I. Schuster, Chem. Eur. J. 2005, 11, 3375.
-
(2005)
Chem. Eur. J
, vol.11
, pp. 3375
-
-
Vail, S.A.1
Krawczuk, P.J.2
Guldi, D.M.3
Palkar, A.4
Echegoyen, L.5
Tome, J.P.6
Fazio, M.A.7
Schuster, D.I.8
-
67
-
-
84985580906
-
-
H. Hofmeister, K. Annen, H. Laurent, R. Wiechert, Angew. Chem. Int. Ed. Engl. 1984, 23, 727.
-
(1984)
Angew. Chem. Int. Ed. Engl
, vol.23
, pp. 727
-
-
Hofmeister, H.1
Annen, K.2
Laurent, H.3
Wiechert, R.4
-
68
-
-
0034647707
-
-
1H NMR spectra. The assignment of relative stereochemistry on the basis of the observed coupling constant for methine protons 3-H and 4-H is a very well-established criterion in β-lactam chemistry. See, for example: B. Alcaide, P. Almendros, N. R. Salgado, A. Rodríguez-Vicente, J. Org. Chem. 2000, 65, 4453.
-
1H NMR spectra. The assignment of relative stereochemistry on the basis of the observed coupling constant for methine protons 3-H and 4-H is a very well-established criterion in β-lactam chemistry. See, for example: B. Alcaide, P. Almendros, N. R. Salgado, A. Rodríguez-Vicente, J. Org. Chem. 2000, 65, 4453.
-
-
-
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