-
2
-
-
33748918437
-
-
(b) Hummel, G.; Reineke, U.; Reimer, U. Mol. BioSyst. 2006, 2, 499-508.
-
(2006)
Mol. BioSyst.
, vol.2
, pp. 499-508
-
-
Hummel, G.1
Reineke, U.2
Reimer, U.3
-
3
-
-
33745181229
-
-
(c) Che, Y.; Brooks, B. R.; Marshall, G. R. J. Comput. Aided Mol. Des. 2006, 20, 109-130.
-
(2006)
J. Comput. Aided Mol. Des.
, vol.20
, pp. 109-130
-
-
Che, Y.1
Brooks, B.R.2
Marshall, G.R.3
-
4
-
-
44949231073
-
-
(d) Vagner, J.; Qu, H.; Hruby, V. J. Curr. Opin. Chem. Biol. 2008, 12, 292-296.
-
(2008)
Curr. Opin. Chem. Biol.
, vol.12
, pp. 292-296
-
-
Vagner, J.1
Qu, H.2
Hruby, V.J.3
-
5
-
-
0030768259
-
-
For reviews, see
-
For reviews, see: (a) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854.
-
(1997)
Tetrahedron
, vol.53
, pp. 12789-12854
-
-
Hanessian, S.1
McNaughton-Smith, G.2
Lombart, H.-G.3
Lubell, W.D.4
-
7
-
-
3943071680
-
-
(c) Belvisi, L.; Colombo, L.; Manzoni, L.; Potenza, D.; Scolastico, C. Synlett 2004, 1449-1471.
-
(2004)
Synlett
, pp. 1449-1471
-
-
Belvisi, L.1
Colombo, L.2
Manzoni, L.3
Potenza, D.4
Scolastico, C.5
-
12
-
-
0032820462
-
-
(a) Belvisi, L.; Gennari, C.; Mielgo, A.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 1999, 389-400.
-
(1999)
Eur. J. Org. Chem.
, pp. 389-400
-
-
Belvisi, L.1
Gennari, C.2
Mielgo, A.3
Potenza, D.4
Scolastico, C.5
-
13
-
-
0038281274
-
-
(b) Vass, E.; Hollósi, M.; Besson, F.; Buchet, R. Chem. Rev. 2003, 103, 1917-1954.
-
(2003)
Chem. Rev.
, vol.103
, pp. 1917-1954
-
-
Vass, E.1
Hollósi, M.2
Besson, F.3
Buchet, R.4
-
14
-
-
64249145893
-
-
For recent examples, see
-
For recent examples, see: (a) Sañudo, M.; García-Valverde, M.; Marcaccini, S.; Delgado, J. J.; Rojo, J.; Torroba, T. J. Org. Chem. 2009, 74, 2189-2192.
-
(2009)
J. Org. Chem.
, vol.74
, pp. 2189-2192
-
-
Sañudo, M.1
García-Valverde, M.2
Marcaccini, S.3
Delgado, J.J.4
Rojo, J.5
Torroba, T.6
-
15
-
-
64249170008
-
-
(b) Li, Y.; Yu, Y.; Giulianotti, M.; Houghten, R. A. J. Org. Chem. 2009, 74, 2183-2185.
-
(2009)
J. Org. Chem.
, vol.74
, pp. 2183-2185
-
-
Li, Y.1
Yu, Y.2
Giulianotti, M.3
Houghten, R.A.4
-
16
-
-
60849087692
-
-
(c) Scheffelaar, R.; Nijenhuis, R. A. K.; Paravidino, M.; Lutz, M.; Spek, A. L.; Ehlers, A. W.; de Kanter, F. J. J.; Groen, M. B.; Orru, R. V. A.; Ruijter, E. J. Org. Chem. 2009, 74, 660-668.
-
(2009)
J. Org. Chem.
, vol.74
, pp. 660-668
-
-
Scheffelaar, R.1
Nijenhuis, R.A.K.2
Paravidino, M.3
Lutz, M.4
Spek, A.L.5
Ehlers, A.W.6
De Kanter, F.J.J.7
Groen, M.B.8
Orru, R.V.A.9
Ruijter, E.10
-
18
-
-
40149107624
-
-
(e) Angell, Y.; Chen, D.; Saragovi, H. U.; Burgess, K. J. Am. Chem. Soc. 2008, 130, 556-565.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 556-565
-
-
Angell, Y.1
Chen, D.2
Saragovi, H.U.3
Burgess, K.4
-
19
-
-
43449130074
-
-
(f) Lomlin, L.; Einsiedel, J.; Heinemann, F. W.; Meyer, K.; Gmeiner, P. J. Org. Chem. 2008, 73, 3608-3611.
-
(2008)
J. Org. Chem.
, vol.73
, pp. 3608-3611
-
-
Lomlin, L.1
Einsiedel, J.2
Heinemann, F.W.3
Meyer, K.4
Gmeiner, P.5
-
20
-
-
57549091464
-
-
(g) Verdié, P.; Subra, G.; Averland-Petit, M.-C.; Amblard, M.; Martinez, J. J. Comb. Chem. 2008, 10, 869-874.
-
(2008)
J. Comb. Chem.
, vol.10
, pp. 869-874
-
-
Verdié, P.1
Subra, G.2
Averland-Petit, M.-C.3
Amblard, M.4
Martinez, J.5
-
21
-
-
55549113866
-
-
(h) Lesma, G.; Colombo, A.; Sacchetti, A.; Silvani, A. Tetrahedron Lett. 2008, 49, 7423-7425.
-
(2008)
Tetrahedron Lett.
, vol.49
, pp. 7423-7425
-
-
Lesma, G.1
Colombo, A.2
Sacchetti, A.3
Silvani, A.4
-
22
-
-
33846449122
-
-
(i) Palomo, C.; Aizpurua, J. M.; Balentová, E.; Jiménez, A.; Oyarbide, J.; Fratila, R. M.; Miranda, J. I. Org. Lett. 2007, 9, 101-104.
-
(2007)
Org. Lett.
, vol.9
, pp. 101-104
-
-
Palomo, C.1
Aizpurua, J.M.2
Balentová, E.3
Jiménez, A.4
Oyarbide, J.5
Fratila, R.M.6
Miranda, J.I.7
-
23
-
-
0035959447
-
-
For reviews, see: (j)
-
For reviews, see: (j) Souers, A. J.; Ellman, J. A. Tetrahedron 2001, 57, 7431-7448.
-
(2001)
Tetrahedron
, vol.57
, pp. 7431-7448
-
-
Souers, A.J.1
Ellman, J.A.2
-
26
-
-
33846060813
-
-
(m) Pérez de Vega, M. J.; Martín-Martínez, M.; González-Muñiz, R. Curr. Top. Med. Chem. 2007, 7, 33-62.
-
(2007)
Curr. Top. Med. Chem.
, vol.7
, pp. 33-62
-
-
De Pérez Vega, M.J.1
Martín-Martínez, M.2
González-Muñiz, R.3
-
27
-
-
37849005357
-
-
(a) Tömböly, C.; Ballet, S.; Feytens, D.; Kövér, K. E.; Borics, A.; Lovas, S.; Al-Khrasani, M.; Fürst, Z.; Tóth, G.; Benhye, S.; Tourwé, D. J. Med. Chem. 2008, 51, 173-177.
-
(2008)
J. Med. Chem.
, vol.51
, pp. 173-177
-
-
Tömböly, C.1
Ballet, S.2
Feytens, D.3
Kövér, K.E.4
Borics, A.5
Lovas, S.6
Al-Khrasani, M.7
Fürst, Z.8
Tóth, G.9
Benhye, S.10
Tourwé, D.11
-
28
-
-
37349031106
-
-
(b) Vartak, A. P.; Skoblenick, K.; Thomas, N.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 2007, 50, 6725-6729.
-
(2007)
J. Med. Chem.
, vol.50
, pp. 6725-6729
-
-
Vartak, A.P.1
Skoblenick, K.2
Thomas, N.3
Mishra, R.K.4
Johnson, R.L.5
-
29
-
-
1542725948
-
-
(c) Cai, M.; Cai, C.; Mayorov, A. V.; Xiong, C.; Cabello, C. M.; Soloshonok, V. A.; Swift, J. R.; Trivedi, D.; Hruby, V. J. J. Peptide Res. 2004, 63, 116-131.
-
(2004)
J. Peptide Res.
, vol.63
, pp. 116-131
-
-
Cai, M.1
Cai, C.2
Mayorov, A.V.3
Xiong, C.4
Cabello, C.M.5
Soloshonok, V.A.6
Swift, J.R.7
Trivedi, D.8
Hruby, V.J.9
-
30
-
-
0035825086
-
-
(d) Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 145-148
-
-
Qiu, W.1
Gu, X.2
Soloshonok, V.A.3
Carducci, M.D.4
Hruby, V.J.5
-
31
-
-
0019163001
-
-
(a) Freidinger, R. M.; Veber, D. F.; Perlow, D. S.; Brooks, J. R.; Saperstein, R. Science 1980, 210, 656-658.
-
(1980)
Science
, vol.210
, pp. 656-658
-
-
Freidinger, R.M.1
Veber, D.F.2
Perlow, D.S.3
Brooks, J.R.4
Saperstein, R.5
-
33
-
-
3142746084
-
-
For previous synthetic approaches to molecules related to 1, see
-
For previous synthetic approaches to molecules related to 1, see:(a) Westermann, B.; Diedrichs, N.; Krelaus, R.; Walter, A.; Gedrath, I. Tetrahedron Lett. 2004, 45, 5983-5986.
-
(2004)
Tetrahedron Lett.
, vol.45
, pp. 5983-5986
-
-
Westermann, B.1
Diedrichs, N.2
Krelaus, R.3
Walter, A.4
Gedrath, I.5
-
34
-
-
13244277648
-
-
(b) Cordero, F. M.; Pisaneschi, F.; Meschini Batista, K.; Valenza, S.; Machetti, F.; Brandi, A. J. Org. Chem. 2005, 70, 856-867.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 856-867
-
-
Cordero, F.M.1
Pisaneschi, F.2
Meschini Batista, K.3
Valenza, S.4
Machetti, F.5
Brandi, A.6
-
35
-
-
22544458508
-
-
(c) Verbist, B. M. P.; De Borggraeve, W. M.; Toppet, S.; Compernolle, F.; Hoornaert, G. J. Eur. J. Org. Chem. 2005, 2941-2950.
-
(2005)
Eur. J. Org. Chem.
, pp. 2941-2950
-
-
Verbist, B.M.P.1
De Borggraeve, W.M.2
Toppet, S.3
Compernolle, F.4
Hoornaert, G.J.5
-
36
-
-
53849110901
-
-
The use of metathesis reactions in peptidomimetic synthesis has been recently reviewed; see
-
The use of metathesis reactions in peptidomimetic synthesis has been recently reviewed; see: (a) Brik, A. Adv. Synth. Catal. 2008, 350, 1661-1675.
-
(2008)
Adv. Synth. Catal.
, vol.350
, pp. 1661-1675
-
-
Brik, A.1
-
37
-
-
0032513726
-
-
For selected examples, see
-
For selected examples, see: (b) Fink, B. E.; Kym, P. R.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1998, 120, 4334-4344.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 4334-4344
-
-
Fink, B.E.1
Kym, P.R.2
Katzenellenbogen, J.A.3
-
38
-
-
0035903517
-
-
(c) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem., Int. Ed. 2001, 40, 3361-3364.
-
(2001)
Angew. Chem., Int. Ed.
, vol.40
, pp. 3361-3364
-
-
Hoffmann, T.1
Lanig, H.2
Waibel, R.3
Gmeiner, P.4
-
39
-
-
3242792576
-
-
(d) Creighton, C. J.; Leo, G. C.; Du, Y.; Reitz, A. B. Bioorg. Med. Chem. 2004, 12, 4375-4385.
-
(2004)
Bioorg. Med. Chem.
, vol.12
, pp. 4375-4385
-
-
Creighton, C.J.1
Leo, G.C.2
Du, Y.3
Reitz, A.B.4
-
41
-
-
39749156932
-
-
3 to the lactone moiety. See
-
3 to the lactone moiety. See: Fustero, S.; Albert, L.; Aceña, J. L.; Sanz-Cervera, J. F.; Asensio, A. Org. Lett. 2008, 10, 605-608.
-
(2008)
Org. Lett.
, vol.10
, pp. 605-608
-
-
Fustero, S.1
Albert, L.2
Aceña, J.L.3
Sanz-Cervera, J.F.4
Asensio, A.5
-
42
-
-
0000453017
-
-
Related chiral templates such as Williams' diphenyloxazinones have also been used in the synthesis of quaternary amino acids; see
-
Related chiral templates such as Williams' diphenyloxazinones have also been used in the synthesis of quaternary amino acids; see: Williams, R. M.; Zhai, W. Tetrahedron 1988, 44, 5425-5430.
-
(1988)
Tetrahedron
, vol.44
, pp. 5425-5430
-
-
Williams, R.M.1
Zhai, W.2
-
43
-
-
0031465724
-
-
Macritchie, J. A.; Silcock, A.; Willis, C. L. Tetrahedron: Asymmetry 1997, 8, 3895-3902.
-
(1997)
Tetrahedron: Asymmetry
, vol.8
, pp. 3895-3902
-
-
Macritchie, J.A.1
Silcock, A.2
Willis, C.L.3
-
44
-
-
66249138715
-
-
note
-
The configuration of the new stereogenic center was assumed as depicted according to previous results (see ref 10) and confirmed in subsequent transformations carried out. Moreover, the stereochemical integrity was preserved in the Grignard addition step as determined by chiral HPLC analysis of compounds 4.
-
-
-
-
45
-
-
17444389675
-
-
A diastereoselective radical addition of alkyl groups to iminolactones 3 was also reported; see
-
A diastereoselective radical addition of alkyl groups to iminolactones 3 was also reported; see: Miyabe, H.; Yamaoka, Y.; Takemoto, Y. J. Org. Chem. 2005, 70, 3324-3327.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 3324-3327
-
-
Miyabe, H.1
Yamaoka, Y.2
Takemoto, Y.3
-
46
-
-
33846138331
-
-
For the synthesis of a trifluoromethyl analogue of 4c, see
-
For the synthesis of a trifluoromethyl analogue of 4c, see: Chaume, G.; Van Severen, M.-C.; Marinkovic, S.; Brigaud, T. Org. Lett. 2006, 8, 6123-6126.
-
(2006)
Org. Lett.
, vol.8
, pp. 6123-6126
-
-
Chaume, G.1
Van Severen, M.-C.2
Marinkovic, S.3
Brigaud, T.4
-
47
-
-
66249104543
-
-
note
-
4, Grubbs-Hoveyda catalyst, or heating under microwave irradiation. In all cases the starting material was recovered unchanged.
-
-
-
-
48
-
-
0035966178
-
-
Preparation of five-membered lactams fused with other rings by means of RCM are very scarce in the literature; see
-
Preparation of five-membered lactams fused with other rings by means of RCM are very scarce in the literature; see: (a) Lim, S. H.; Ma, S.; Beak, P. J. Org. Chem. 2001, 66, 9056-9062.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 9056-9062
-
-
Lim, S.H.1
Ma, S.2
Beak, P.3
-
49
-
-
40649123784
-
-
(b) Muroni, D.; Mucedda, M.; Saba, A. Tetrahedron Lett. 2008, 49, 2373-2376.
-
(2008)
Tetrahedron Lett.
, vol.49
, pp. 2373-2376
-
-
Muroni, D.1
Mucedda, M.2
Saba, A.3
-
50
-
-
66249144555
-
-
note
-
Direct coupling of amine 4a with a N-Boc-protected dehydroalanine failed to provide a RCM precursor of compound 11. (Chemical Equation Presented)
-
-
-
-
51
-
-
66249127092
-
-
note
-
Base-mediated transesterification or hydrogenolysis at high pressure of the lactone ring in 12 failed to give the corresponding hydroxy ester or hydroxy acid.
-
-
-
-
52
-
-
0028867825
-
-
Related seven-membered lactams were prepared by Holmes and coworkers, although lacking the quaternary center. In their work, the cis diastereoisomer had an extended conformation, whereas the trans isomer formed a β-turn structure. See
-
Related seven-membered lactams were prepared by Holmes and coworkers, although lacking the quaternary center. In their work, the cis diastereoisomer had an extended conformation, whereas the trans isomer formed a β-turn structure. See: Nadin, A.; Derrer, S.; McGeary, R. P.; Goodman, J. M.; Raithby, P. R.; Holmes, A. B.; O'Hanlon, P. J.; Pearson, N. D. J. Am. Chem. Soc. 1995, 117, 9768-9769.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 9768-9769
-
-
Nadin, A.1
Derrer, S.2
McGeary, R.P.3
Goodman, J.M.4
Raithby, P.R.5
Holmes, A.B.6
O'Hanlon, P.J.7
Pearson, N.D.8
|