-
3
-
-
14844362964
-
-
b) J. F. Fisher, S.O. Meroueh, S. Mobashery, Chem. Rev. 2005, 105, 395;
-
(2005)
Chem. Rev.
, vol.105
, pp. 395
-
-
Fisher, J.F.1
Meroueh, S.O.2
Mobashery, S.3
-
6
-
-
0001117281
-
-
(Ed.: G. Lukacs), Springer, Berlin
-
e) 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, p621;
-
(1993)
Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products
, vol.2
, pp. 621
-
-
Branch, S.C.1
Coulton, S.2
Hunt, E.3
-
7
-
-
0004030275
-
-
(Ed.: M. I. Page), Chapman and Hall: London
-
f) The Chemistry of β-Lactams, (Ed.: M. I. Page), Chapman and Hall: London, 1992;
-
(1992)
The Chemistry of β-Lactams
-
-
-
8
-
-
0004030277
-
-
(Eds. : R. B. Morin, M. Gorman), Academic, New York
-
g) Chemistry and Biology of β-Lactam Antibiotics, (Eds. : R. B. Morin, M. Gorman), Academic, New York, 1982, Vols. 1-3.
-
(1982)
Chemistry and Biology of β-Lactam Antibiotics
, vol.1-3
-
-
-
9
-
-
36849034419
-
-
For selected reviews on 2-azetidinones acting as an important class of organic intermediates in organic synthesis, see: a) B. Alcaide, R Almendros, C. Aragoncillo, Chem. Rev. 2007, 107, 4437;
-
(2007)
Chem. Rev.
, vol.107
, pp. 4437
-
-
Alcaide, B.1
Almendros, R.2
Aragoncillo, C.3
-
11
-
-
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
-
13
-
-
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
-
17
-
-
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
-
19
-
-
35348917610
-
-
b) K. L. Curtis, E. L. Evinson, S. Handa, K. Singh, Org. Biomol. Chem. 2007, 5, 3544;
-
(2007)
Org. Biomol. Chem.
, vol.5
, pp. 3544
-
-
Curtis, K.L.1
Evinson, E.L.2
Handa, S.3
Singh, K.4
-
22
-
-
0034607947
-
-
e) N. Asano, R. J. Nash, R. J. Molyneux, G. J. J Fleet, Tetrahedron: Asymmetry 2000, 11, 1645;
-
(2000)
Tetrahedron: Asymmetry
, vol.11
, pp. 1645
-
-
Asano, N.1
Nash, R.J.2
Molyneux, R.J.3
Fleet, G.J.J.4
-
24
-
-
56849088735
-
-
For recent reviews, see: a) S. Das, R. Borah, R. R. Devi, A. J. Thakur, Synlett 2008, 2741;
-
(2008)
Synlett
, pp. 2741
-
-
Das, S.1
Borah, R.2
Devi, R.R.3
Thakur, A.J.4
-
26
-
-
85057634353
-
-
a) B. Alcaide, P. Almendros, G. Cabrero, M. P. Ruiz, Chem. Commun. 2008, 615;
-
(2008)
Chem. Commun.
, pp. 615
-
-
Alcaide, B.1
Almendros, P.2
Cabrero, G.3
Ruiz, M.P.4
-
27
-
-
51949118124
-
-
b) B. Alcaide, P. Almendros, G. Cabrero, M. P. Ruiz, Synthesis 2008, 2835.
-
(2008)
Synthesis
, pp. 2835
-
-
Alcaide, B.1
Almendros, P.2
Cabrero, G.3
Ruiz, M.P.4
-
28
-
-
35348912513
-
-
We have recently described the hydrocyanation and cyanosilylation of 4-oxoazetidine-2-carbaldehydes together with the manipulation of the corresponding β-lactam cyanohydrins: B. Alcaide, P. Almendros, G. Cabrero, M. P. Ruiz, J. Org. Chem. 2007, 72, 7980.
-
(2007)
J. Org. Chem.
, vol.72
, pp. 7980
-
-
-
30
-
-
64349109494
-
-
c) S. Dekeukeleire, M. D'hooghe, N. De Kimpe, J. Org. Chem. 2009, 74, 1644.
-
(2009)
J. Org. Chem.
, vol.74
, pp. 1644
-
-
Dekeukeleire, S.1
D'Hooghe, M.2
De Kimpe, N.3
-
31
-
-
77952725353
-
-
See, for instance: a) B. Alcaide, P. Almendros, R. Carrascosa, M. R. Torres, Adv. Synth. Catal. 2010, 352, 1277;
-
(2010)
Adv. Synth. Catal.
, vol.352
, pp. 1277
-
-
Alcaide, B.1
Almendros, P.2
Carrascosa, R.3
Torres, M.R.4
-
32
-
-
77949860743
-
-
b) B. Alcaide, P. Almendros, A. Luna, M. R. Torres, Adv. Synth. Catal. 2010, 352, 621;
-
(2010)
Adv. Synth. Catal.
, vol.352
, pp. 621
-
-
Alcaide, B.1
Almendros, P.2
Luna, A.3
Torres, M.R.4
-
33
-
-
63749122772
-
-
c) B. Alcaide, P. Almendros, T. Martínez del Campo, M. T. Quirós, Chem. Eur. J. 2009, 15, 3344;
-
(2009)
Chem. Eur. J
, vol.15
, pp. 3344
-
-
Alcaide, B.1
Almendros, P.2
Martínez Del Campo, T.3
Quirós, M.T.4
-
34
-
-
62349125016
-
-
(d) B. Alcaide, P. Almendros, R. Carrascosa, T. Martínez del Campo, Chem. Eur. J. 2009, 15, 2496;
-
(2009)
Chem. Eur. J
, vol.15
, pp. 2496
-
-
Alcaide, B.1
Almendros, P.2
Carrascosa, R.3
Martínez Del Campo, T.4
-
35
-
-
38149116921
-
-
e) B. Alcaide, P. Almendros, R. Carrascosa, M. C. Redondo, Chem. Eur. J. 2008, 14, 637;
-
(2008)
Chem. Eur. J
, vol.14
, pp. 637
-
-
Alcaide, B.1
Almendros, P.2
Carrascosa, R.3
Redondo, M.C.4
-
36
-
-
53649110016
-
-
f) B. Alcaide, P. Almendros, T. Martínez del Campo, Angew. Chem. 2007, 119, 6804;
-
(2007)
Angew. Chem.
, vol.119
, pp. 6804
-
-
Alcaide, B.1
Almendros, P.2
Martínez Del Campo, T.3
-
38
-
-
72049088291
-
-
a) B. Das, P. Balasubramanyam, M. Krishnaiah, B. Veeranjaneyulu, G. C. Reddy, Synthesis 2009, 3467;
-
(2009)
Synthesis
, pp. 3467
-
-
Das, B.1
Balasubramanyam, P.2
Krishnaiah, M.3
Veeranjaneyulu, B.4
Reddy, G.C.5
-
39
-
-
0037164649
-
-
b) J. S. Yadav, B. V. S. Reddy, M. S. Reddy, A. R. Prasad, Tetrahedron Lett. 2002, 43, 9703.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 9703
-
-
Yadav, J.S.1
Reddy, B.V.S.2
Reddy, M.S.3
Prasad, A.R.4
-
41
-
-
0001318920
-
-
D. R. Wagle, C. Garai, J. Chiang, M. G. Monteleone, B. E. Kurys, T. W. Strohmeyer, V. R. Hedge, M. S. Manhas, A. K. Bose, J. Org. Chem. 1988, 53, 4227.
-
(1988)
J. Org. Chem.
, vol.53
, pp. 4227
-
-
Wagle, D.R.1
Garai, C.2
Chiang, J.3
Monteleone, M.G.4
Kurys, B.E.5
Strohmeyer, T.W.6
Hedge, V.R.7
Manhas, M.S.8
Bose, A.K.9
-
42
-
-
68249087887
-
-
The pyroglutamic acid core has considerable chemical and medicinal importance as it is involved in a wide range of relevant processes. For reviews, see: a) S. K. Panday, J. Prasad, D. K. Dikshit, Tetrahedron: Asymmetry 2009, 20, 1581;
-
(2009)
Tetrahedron: Asymmetry
, vol.20
, pp. 1581
-
-
Panday, S.K.1
Prasad, J.2
Dikshit, D.K.3
-
44
-
-
0037064592
-
-
M. Oba, S. Koguchi, K. Nishiyama, Tetrahedron 2002, 58, 9359.
-
(2002)
Tetrahedron
, vol.58
, pp. 9359
-
-
Oba, M.1
Koguchi, S.2
Nishiyama, K.3
-
45
-
-
51049123588
-
-
Recently, it has been demonstrated that a cis-5-alkyl-4-hydroxy-2- pyrrolidinone related to 7, named as streptopyrrolidine and isolated from a marine Streptomyces, blocked the capillary tube formation of the cells at the same potency as a known angiogenesis inhibitor SU11248: H.-J. Shin, T.-S. Kim, H.-S. Lee, J.-Y. Park, I.-K. Choi, H.-J. Kwon, Phytochemistry 2008, 69, 2363.
-
(2008)
Phytochemistry
, vol.69
, pp. 2363
-
-
Shin, H.-J.1
Kim, T.-S.2
Lee, H.-S.3
Park, J.-Y.4
Choi, I.-K.5
Kwon, H.-J.6
-
46
-
-
0034725855
-
-
Tricyclic β-lactam antibiotics which are generally referred to as trinems are a new class of synthetic antibacterial agents featuring good resistance to β-lactamases and dehydropeptidases: a) O. Kanno, I. Kawamoto, Tetrahedron 2000, 56, 5639;
-
(2000)
Tetrahedron
, vol.56
, pp. 5639
-
-
Kanno, O.1
Kawamoto, I.2
-
48
-
-
0001363860
-
The chemistry of trinems
-
(Eds.: O. A. Attanasi, D. Spinelli), Societa Chimica Italiana, Rome, For a review on tricyclic β-lactams, see
-
c) C. Ghiron, T. Rossi, The Chemistry of Trinems, in: Targets in Hetero- cyclic Systems - Chemistry and Properties, (Eds.: O. A. Attanasi, D. Spinelli), Societa Chimica Italiana, Rome, 1997, Vol. 1, pp 161-186. For a review on tricyclic β-lactams, see:
-
(1997)
Targets in Hetero- Cyclic Systems - Chemistry and Properties
, vol.1
, pp. 161-186
-
-
Ghiron, C.1
Rossi, T.2
-
50
-
-
0000818237
-
-
(Eds.: B. M. Trost, I. Fleming), Pergamon Press, New York
-
R. Bishop, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Pergamon Press, New York, 1991, Vol. 6, pp 261-300.
-
(1991)
Comprehensive Organic Synthesis
, vol.6
, pp. 261-300
-
-
Bishop, R.1
-
51
-
-
73349122613
-
-
Little information regarding this type of oxygen-containing 3,4-fused β-lactam systems can be found in the literature. For selected examples, see: a) E. Leemans, M. D'hooghe, Y. Dejaegher, K. W. Törnroos, N. De Kimpe, Eur. J. Org. Chem. 2010, 352;
-
(2010)
Eur. J. Org. Chem.
, pp. 352
-
-
Leemans, E.1
D'Hooghe, M.2
Dejaegher, Y.3
Törnroos, K.W.4
De Kimpe, N.5
-
52
-
-
76349093633
-
-
b) Z. Zhang, Q. Zhang, Z. Ni, Q. Liu, Chem. Commun. 2010, 46, 1269;
-
(2010)
Chem. Commun.
, vol.46
, pp. 1269
-
-
Zhang, Z.1
Zhang, Q.2
Ni, Z.3
Liu, Q.4
-
53
-
-
60749096548
-
-
c) B. Alcaide, P. Almendros, T. Martínez del Campo, E. Soriano, J. L. Marco-Contelles, Chem. Eur. J. 2009, 15, 1901;
-
(2009)
Chem. Eur. J
, vol.15
, pp. 1901
-
-
Alcaide, B.1
Almendros, P.2
Martínez Del Campo, T.3
Soriano, E.4
Marco-Contelles, J.L.5
-
54
-
-
70350514479
-
-
d) A. Al-Harrasi, F. Pfrengle, V. Prisyazhnyuk, S. Yekta, P. Koóš, H.-U Reissig, Chem. Eur. J. 2009, 15, 11632;
-
(2009)
Chem. Eur. J
, vol.15
, pp. 11632
-
-
Al-Harrasi, A.1
Pfrengle, F.2
Prisyazhnyuk, V.3
Yekta, S.4
Koóš, P.5
Reissig, H.-U.6
-
55
-
-
14344259400
-
-
e) P. Del Buttero, G. Molteni, A. Papagni, T. Pilati, Tetrahedron: Asymmetry 2005, 16, 971.
-
(2005)
Tetrahedron: Asymmetry
, vol.16
, pp. 971
-
-
Del Buttero, P.1
Molteni, G.2
Papagni, A.3
Pilati, T.4
-
58
-
-
0030756832
-
-
b) L. R. Domingo, J. Andres, V. Moliner, V. S. Safont, J. Am. Chem. Soc. 1997, 119, 6415.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 6415
-
-
Domingo, L.R.1
Andres, J.2
Moliner, V.3
Safont, V.S.4
-
59
-
-
33847114330
-
-
M. Arnó, R. J. Zaragoza, L. R. Domingo, Tetrahedron: Asymmetry 2007, 18, 157.
-
(2007)
Tetrahedron: Asymmetry
, vol.18
, pp. 157
-
-
Arnó, M.1
Zaragoza, R.J.2
Domingo, L.R.3
-
61
-
-
77954774532
-
-
Experimental procedures as well as full spectroscopic and analytical data for compounds not included in this Experimental Section are described in the Supporting Information. It contains as well copies of NMR spectra for all new compounds
-
Experimental procedures as well as full spectroscopic and analytical data for compounds not included in this Experimental Section are described in the Supporting Information. It contains as well copies of NMR spectra for all new compounds.
-
-
-
-
63
-
-
0345491105
-
-
b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
-
(1988)
Phys. Rev. B
, vol.37
, pp. 785
-
-
Lee, C.1
Yang, W.2
Parr, R.G.3
-
64
-
-
84873055189
-
-
Wiley, New York
-
W. J. Hehre, L. Radom, P. v. R. Schleyer, J. A. Pople, Ab initio Molecular Orbital Theory, Wiley, New York, 1986.
-
(1986)
Ab Initio Molecular Orbital Theory
-
-
Hehre, W.J.1
Radom, L.2
Schleyer, P.V.R.3
Pople, J.A.4
-
65
-
-
0031209054
-
-
a) E. Canees, B. Mennucci, J. Tomasi, J. Chem. Phys. 1997, 107, 3032;
-
(1997)
J. Chem. Phys.
, vol.107
, pp. 3032
-
-
Canees, E.1
Mennucci, B.2
Tomasi, J.3
-
66
-
-
84962359221
-
-
b) M. Cossi, V. Barone, R. Cammi, J. Tomasi, Chem. Phys. Lett. 1996, 255, 327;
-
(1996)
Chem. Phys. Lett.
, vol.255
, pp. 327
-
-
Cossi, M.1
Barone, V.2
Cammi, R.3
Tomasi, J.4
-
67
-
-
84962428785
-
-
c) V. Barone, M. Cossi, J. Tomasi, J. Comput. Chem. 1998, 19, 404.
-
(1998)
J. Comput. Chem.
, vol.19
, pp. 404
-
-
Barone, V.1
Cossi, M.2
Tomasi, J.3
-
69
-
-
0010789049
-
-
(Ed.: D. R. Yarkony), World Scientific Publishing, Singapore
-
b) H. B. Schlegel, Geometry Optimization on Potential Energy Surface, in: Modern Electronic Structure Theory, (Ed.: D. R. Yarkony), World Scientific Publishing, Singapore, 1994.
-
(1994)
Geometry Optimization on Potential Energy Surface, In: Modern Electronic Structure Theory
-
-
Schlegel, H.B.1
-
73
-
-
36148995600
-
-
a) A. E. Reed, R. B. Weinstock, F. Weinhold, J. Chem. Phys. 1985, 83, 735;
-
(1985)
J. Chem. Phys.
, vol.83
, pp. 735
-
-
Reed, A.E.1
Weinstock, R.B.2
Weinhold, F.3
-
74
-
-
0011083499
-
-
b) A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899.
-
(1988)
Chem. Rev.
, vol.88
, pp. 899
-
-
Reed, A.E.1
Curtiss, L.A.2
Weinhold, F.3
-
75
-
-
0038626673
-
-
Gaussian, Inc., Wallingford CT
-
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, T. Vreven, K. N. Kudin, J. C Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Gaussian, Inc., Wallingford CT, 2004.
-
(2004)
Gaussian 03
-
-
Frisch, M.J.1
Trucks, G.W.2
Schlegel, H.B.3
Scuseria, G.E.4
Robb, M.A.5
Cheeseman, J.R.6
Montgomery, J.A.7
Vreven, T.8
Kudin, K.N.9
Burant, J.C.10
Millam, J.M.11
Iyengar, S.S.12
Tomasi, J.13
Barone, V.14
Mennucci, B.15
Cossi, M.16
Scalmani, G.17
Rega, N.18
Petersson, G.A.19
Nakatsuji, H.20
Hada, M.21
Ehara, M.22
Toyota, K.23
Fukuda, R.24
Hasegawa, J.25
Ishida, M.26
Nakajima, T.27
Honda, Y.28
Kitao, O.29
Nakai, H.30
Klene, M.31
Li, X.32
Knox, J.E.33
Hratchian, H.P.34
Cross, J.B.35
Adamo, C.36
Jaramillo, J.37
Gomperts, R.38
Stratmann, R.E.39
Yazyev, O.40
Austin, A.J.41
Cammi, R.42
Pomelli, C.43
Ochterski, J.W.44
Ayala, P.Y.45
Morokuma, K.46
Voth, G.A.47
Salvador, P.48
Dannenberg, J.J.49
Zakrzewski, V.G.50
Dapprich, S.51
Daniels, A.D.52
Strain, M.C.53
Farkas, O.54
Malick, D.K.55
Rabuck, A.D.56
Raghavachari, K.57
Foresman, J.B.58
Ortiz, J.V.59
Cui, Q.60
Baboul, A.G.61
Clifford, S.62
Cioslowski, J.63
Stefanov, B.B.64
Liu, G.65
Liashenko, A.66
Piskorz, P.67
Komaromi, I.68
Martin, R.L.69
Fox, D.J.70
Keith, T.71
Al-Laham, M.A.72
Peng, C.Y.73
Nanayakkara, A.74
Challacombe, M.75
Gill, P.M.W.76
Johnson, B.77
Chen, W.78
Wong, M.W.79
Gonzalez, C.80
Pople, J.A.81
more..
|