-
1
-
-
0036291655
-
-
Step economy: a P. A. Wender, F. C. Bi, G. G. Gamber, F. Gosselin, R. D. Hubbard, M. J. C. Scanio, R. Sun, T. J. Williams, L. Zhang, Pure Appl. Chem. 2002, 74, 25-31;
-
Step economy: a) P. A. Wender, F. C. Bi, G. G. Gamber, F. Gosselin, R. D. Hubbard, M. J. C. Scanio, R. Sun, T. J. Williams, L. Zhang, Pure Appl. Chem. 2002, 74, 25-31;
-
-
-
-
2
-
-
0037313008
-
-
b) P. A. Wender, J. L. Baryza, S. E. Brenner, M. O. Clarke, G. G. Gamber, J. C. Horan, T. C. Jessop, C. Kan, K. Pattabiraman, T. J. Williams, Pure Appl. Chem. 2003, 75, 143-155;
-
(2003)
Pure Appl. Chem
, vol.75
, pp. 143-155
-
-
Wender, P.A.1
Baryza, J.L.2
Brenner, S.E.3
Clarke, M.O.4
Gamber, G.G.5
Horan, J.C.6
Jessop, T.C.7
Kan, C.8
Pattabiraman, K.9
Williams, T.J.10
-
3
-
-
4644248644
-
-
c) P. A. Wender, J. L. Baryza, S. E. Brenner, M. O. Clarke, M. L. Craske, J. C. Horan, T. Meyer, Curr. Drug Discovery Technol. 2004, 1, 1-11;
-
(2004)
Curr. Drug Discovery Technol
, vol.1
, pp. 1-11
-
-
Wender, P.A.1
Baryza, J.L.2
Brenner, S.E.3
Clarke, M.O.4
Craske, M.L.5
Horan, J.C.6
Meyer, T.7
-
4
-
-
14844290896
-
-
d) P. A. Wender, G. G. Gamber, R. D. Hubbard, S. M. Pham, L. Zhang, J. Am. Chem. Soc. 2005, 127, 2836-2837.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 2836-2837
-
-
Wender, P.A.1
Gamber, G.G.2
Hubbard, R.D.3
Pham, S.M.4
Zhang, L.5
-
5
-
-
0026418434
-
-
Atom economy: a B. M. Trost, Science 1991, 254, 1471-1477;
-
Atom economy: a) B. M. Trost, Science 1991, 254, 1471-1477;
-
-
-
-
6
-
-
0000791854
-
-
b) B. M. Trost, Angew. Chem. 1995, 107, 285-287;
-
(1995)
Angew. Chem
, vol.107
, pp. 285-287
-
-
Trost, B.M.1
-
7
-
-
33750309194
-
-
Angew. Chem. Int. Ed. 1995, 34, 259-281;
-
(1995)
Angew. Chem. Int. Ed
, vol.34
, pp. 259-281
-
-
-
9
-
-
34447094656
-
-
For a recent special issue on green chemistry see Chem. Rev. 2007, 107, 2167-2820.
-
For a recent special issue on green chemistry see Chem. Rev. 2007, 107, 2167-2820.
-
-
-
-
10
-
-
84890597202
-
-
For a recent monograph see:, Eds, J. Zhu, H. Bienaymé, Wiley-VCH, Weinheim
-
a) For a recent monograph see: Multicomponent Reactions (Eds.: J. Zhu, H. Bienaymé). Wiley-VCH, Weinheim, 2005;
-
(2005)
Multicomponent Reactions
-
-
-
11
-
-
33745795702
-
-
for a special issue on
-
b) for a special issue on MCRs see Tetrahedron 2005, 61, 11299-11519;
-
(2005)
Tetrahedron
, vol.61
, pp. 11299-11519
-
-
MCRs see1
-
12
-
-
0034665244
-
-
for some recent reviews of MCRs see: c H. Bienaymé. G Hulme, C. Oddon, P. Schmitt, Chem. Eur. J. 2000, 6, 3321-3329;
-
for some recent reviews of MCRs see: c) H. Bienaymé. G Hulme, C. Oddon, P. Schmitt, Chem. Eur. J. 2000, 6, 3321-3329;
-
-
-
-
14
-
-
0001134412
-
-
Angew. Chem. Int. Ed. 2000, 39, 3168-3210;
-
(2000)
Angew. Chem. Int. Ed
, vol.39
, pp. 3168-3210
-
-
-
18
-
-
17144366282
-
-
Angew. Chem. Int. Ed. 2005, 44, 1602-1634;
-
(2005)
Angew. Chem. Int. Ed
, vol.44
, pp. 1602-1634
-
-
-
19
-
-
31544434530
-
-
h) A. Dömling, Chem. Rev. 2006, 106, 17-89.
-
(2006)
Chem. Rev
, vol.106
, pp. 17-89
-
-
Dömling, A.1
-
20
-
-
7044235263
-
-
For representative reviews see: a
-
For representative reviews see: a) L. F. Tietze, Chem. Rev. 1996, 96, 115-136;
-
(1996)
Chem. Rev
, vol.96
, pp. 115-136
-
-
Tietze, L.F.1
-
23
-
-
84890766709
-
-
for a recent monograph see:, Wiley-VCH, Weinheim
-
d) for a recent monograph see: L. F. Tietze, G. Brasche, K. M. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006.
-
(2006)
Domino Reactions in Organic Synthesis
-
-
Tietze, L.F.1
Brasche, G.2
Gericke, K.M.3
-
24
-
-
0034678033
-
-
For reviews see: a
-
For reviews see: a) S. L. Schreiber, Science 2000, 287, 1964-1969;
-
(2000)
Science
, vol.287
, pp. 1964-1969
-
-
Schreiber, S.L.1
-
26
-
-
33745785038
-
-
c) J. Gerencser, G. Dorman, F. Darvas, QSAR Comb. Sci. 2006, 25, 439-448;
-
(2006)
QSAR Comb. Sci
, vol.25
, pp. 439-448
-
-
Gerencser, J.1
Dorman, G.2
Darvas, F.3
-
29
-
-
33745775855
-
-
b) F. Liéby-Muller, C. Simon, T. Constantieux, J. Rodriguez, QSAR Comb. Sci. 2006, 25, 432-438;
-
(2006)
QSAR Comb. Sci
, vol.25
, pp. 432-438
-
-
Liéby-Muller, F.1
Simon, C.2
Constantieux, T.3
Rodriguez, J.4
-
30
-
-
29044446242
-
-
c) F. Liéby-Muller, T. Constantieux, J. Rodriguez, J. Am. Chem. Soc. 2005, 127, 17176-17177;
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 17176-17177
-
-
Liéby-Muller, F.1
Constantieux, T.2
Rodriguez, J.3
-
31
-
-
34248166450
-
-
d) H. Habib-Zahmani, J. Viala, S. Hacini, J. Rodriguez, Synlett 2007, 1037-1042;
-
(2007)
Synlett
, pp. 1037-1042
-
-
Habib-Zahmani, H.1
Viala, J.2
Hacini, S.3
Rodriguez, J.4
-
34
-
-
0032541716
-
-
For other reports on two-carbon ring expansion of five-membered rings see: a
-
For other reports on two-carbon ring expansion of five-membered rings see: a) M. Miesch, G. Mislin, M. Franck-Neumann, Tetrahedron Lett. 1998, 39, 6873-6876;
-
(1998)
Tetrahedron Lett
, vol.39
, pp. 6873-6876
-
-
Miesch, M.1
Mislin, G.2
Franck-Neumann, M.3
-
37
-
-
34250764873
-
-
Angew. Chem. Int. Ed. 2007, 46, 3966-3970.
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 3966-3970
-
-
-
38
-
-
0033618523
-
-
For reviews see: a
-
For reviews see: a) L. Yet, Tetrahedron 1999, 55, 9349-9403
-
(1999)
Tetrahedron
, vol.55
, pp. 9349-9403
-
-
Yet, L.1
-
39
-
-
0034246704
-
-
and L. Yet, Chem. Rev. 2000, 100, 2963-3007;
-
(2000)
Chem. Rev
, vol.100
, pp. 2963-3007
-
-
Yet, L.1
-
41
-
-
0000402646
-
-
c) M. E. Maier, Angew. Chem. 2000, 112, 2153-2157;
-
(2000)
Angew. Chem
, vol.112
, pp. 2153-2157
-
-
Maier, M.E.1
-
42
-
-
0034674322
-
-
Angew. Chem. Int. Ed. 2000, 39, 2073-2077.
-
(2000)
Angew. Chem. Int. Ed
, vol.39
, pp. 2073-2077
-
-
-
43
-
-
0028810949
-
-
a) M.-H. Filippini, R. Faure, J. Rodriguez, J. Org. Chem. 1995, 60, 6872-6882;
-
(1995)
J. Org. Chem
, vol.60
, pp. 6872-6882
-
-
Filippini, M.-H.1
Faure, R.2
Rodriguez, J.3
-
49
-
-
0001230338
-
-
c) G. L. Buchanan, C. Maxwell, W. Henderson, Tetrahedron 1965, 21, 3273-3276;
-
(1965)
Tetrahedron
, vol.21
, pp. 3273-3276
-
-
Buchanan, G.L.1
Maxwell, C.2
Henderson, W.3
-
52
-
-
0026672841
-
-
f) R. Chakraborty, M. K. Basu, B. C. Ranu, Tetrahedron 1992, 48, 8849-8854.
-
(1992)
Tetrahedron
, vol.48
, pp. 8849-8854
-
-
Chakraborty, R.1
Basu, M.K.2
Ranu, B.C.3
-
53
-
-
34248173879
-
-
For a recent related radical-mediated fragmentation of bicyclo[3.2.1]octanes see: T. K. Pradhan, A. Hassner, Synlett 2007, 1071-1074.
-
For a recent related radical-mediated fragmentation of bicyclo[3.2.1]octanes see: T. K. Pradhan, A. Hassner, Synlett 2007, 1071-1074.
-
-
-
-
54
-
-
33845670735
-
-
For another ring-expansion strategy of cyclic β-ketoesters for the preparation of medium-size rings initiated by conjugated addition see: I. Hachiya, W. Maehara, Y. Yamada, T. Kamiki, M. Shimizu, Synlett 2006, 3271-3274
-
For another ring-expansion strategy of cyclic β-ketoesters for the preparation of medium-size rings initiated by conjugated addition see: I. Hachiya, W. Maehara, Y. Yamada, T. Kamiki, M. Shimizu, Synlett 2006, 3271-3274.
-
-
-
-
55
-
-
53849105688
-
-
CCDC 620411 (4c), 615710 (9), 615708 (15b). 615709 (15c) and 620412 (25c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif
-
CCDC 620411 (4c), 615710 (9), 615708 (15b). 615709 (15c) and 620412 (25c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif
-
-
-
-
59
-
-
0000798527
-
-
A part of these results has been reported in a preliminary communication: M.-H. Filippini, J. Rodriguez, J. Org. Chem. 1997, 62, 3034-3035; the structure of the cycloheplenic acid 8 has been revisited and confirmed to be as depicted in Schemes. The incorrect 1.3-cis stereochemistry previously reported for 8 is a result of the misinterpretation of an artifact on the NOESY spectrum, which indeed clearly shows the 1,3-trans stereochemistry (see discussion).
-
A part of these results has been reported in a preliminary communication: M.-H. Filippini, J. Rodriguez, J. Org. Chem. 1997, 62, 3034-3035; the structure of the cycloheplenic acid 8 has been revisited and confirmed to be as depicted in Schemes. The incorrect 1.3-cis stereochemistry previously reported for 8 is a result of the misinterpretation of an artifact on the NOESY spectrum, which indeed clearly shows the 1,3-trans stereochemistry (see discussion).
-
-
-
-
61
-
-
53849123564
-
-
The enthalpies of formation, which were kindly provided by one of lhe reviewers of reference [18] and calculated with PCMODEL for both 1,3-cis and 1,3-trans isomers of 8a, corroborate our own results obtained from AM1/RHF (AMPAC) semiempirical calculations and showed a preference of 1.1-2.2 kcal in favour of the 1.3-cis-diequatorial isomer, which corresponds to an approximate 80:20 to 95:5 mixture (1,3-cis major) if thermodynamic equilibrium is achieved. See the Supporling Information.
-
The enthalpies of formation, which were kindly provided by one of lhe reviewers of reference [18] and calculated with PCMODEL for both 1,3-cis and 1,3-trans isomers of 8a, corroborate our own results obtained from AM1/RHF (AMPAC) semiempirical calculations and showed a preference of 1.1-2.2 kcal in favour of the 1.3-cis-diequatorial isomer, which corresponds to an approximate 80:20 to 95:5 mixture (1,3-cis major) if thermodynamic equilibrium is achieved. See the Supporling Information.
-
-
-
-
62
-
-
33750519266
-
-
A pari of these results has been reported in a preliminary communication: a Y. Coquerel, D. Bensa, V. Moret, J. Rodriguez, Synlett 2006, 2751-2754;
-
A pari of these results has been reported in a preliminary communication: a) Y. Coquerel, D. Bensa, V. Moret, J. Rodriguez, Synlett 2006, 2751-2754;
-
-
-
-
63
-
-
33845664473
-
-
b) Y. Coquerel, D. Bensa, V. Moret, J. Rodriguez, Synlett 2006, 3368-3368.
-
(2006)
Synlett
, pp. 3368-3368
-
-
Coquerel, Y.1
Bensa, D.2
Moret, V.3
Rodriguez, J.4
-
64
-
-
53849137211
-
-
For the synthesis of 9c see: a S. H. Bertz, J. M. Cook, A. Gawish, U. Weiss, Org. Synth. 1986, 64, 27-37;
-
For the synthesis of 9c see: a) S. H. Bertz, J. M. Cook, A. Gawish, U. Weiss, Org. Synth. 1986, 64, 27-37;
-
-
-
-
66
-
-
33847799030
-
-
B. M. Trost, T. N. Salzmann, K. Hiroi, J. Am. Chem. Soc. 1976, 98, 4887-4902.
-
(1976)
J. Am. Chem. Soc
, vol.98
, pp. 4887-4902
-
-
Trost, B.M.1
Salzmann, T.N.2
Hiroi, K.3
-
67
-
-
37049081677
-
-
M. C. Carreño, J. L. García Ruano, C. Pedregal, A. Rubio, J. Chem. Soc. Perkin Trans. 1 1989, 1335-1337.
-
(1989)
J. Chem. Soc. Perkin Trans. 1
, pp. 1335-1337
-
-
Carreño, M.C.1
García Ruano, J.L.2
Pedregal, C.3
Rubio, A.4
-
68
-
-
0026742502
-
-
a) G. A. Kraus, J. Hansen, D. Vines, Synth. Commun. 1992, 22, 2625-2634;
-
(1992)
Synth. Commun
, vol.22
, pp. 2625-2634
-
-
Kraus, G.A.1
Hansen, J.2
Vines, D.3
-
70
-
-
85004388152
-
-
a) N. Hashimoto, T. Aoyama, T. Shiori, Chem. Pharm. Bull. 1981, 29, 1475-1478;
-
(1981)
Chem. Pharm. Bull
, vol.29
, pp. 1475-1478
-
-
Hashimoto, N.1
Aoyama, T.2
Shiori, T.3
-
71
-
-
53849083347
-
-
for the mechanism see: b
-
for the mechanism see: b) E. Kühnel, D. D. P. Laffan, G. C. Lloyd-Jones, T. Martinez del Campo, I. R. Shepperson, J. L. Slaughter, Angew. Chem. 2007, 119, 7205-7208;
-
(2007)
Angew. Chem
, vol.119
, pp. 7205-7208
-
-
Kühnel, E.1
Laffan, D.D.P.2
Lloyd-Jones, G.C.3
Martinez del Campo, T.4
Shepperson, I.R.5
Slaughter, J.L.6
-
72
-
-
34848822791
-
-
Angew. Chem. Int. Ed. 2007, 46, 7075-7078.
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 7075-7078
-
-
-
73
-
-
53849088107
-
-
2Et. See: a F. G. Bordwell, J. A. Harrelson, Jr., Can. J. Chem. 1990, 68, 1714-1718;
-
2Et. See: a) F. G. Bordwell, J. A. Harrelson, Jr., Can. J. Chem. 1990, 68, 1714-1718;
-
-
-
-
75
-
-
1542502091
-
-
For oxepanes see: a
-
For oxepanes see: a) T. Yasumoto, M. Murata, Chem. Rev. 1993, 93, 1897-1909;
-
(1993)
Chem. Rev
, vol.93
, pp. 1897-1909
-
-
Yasumoto, T.1
Murata, M.2
-
77
-
-
13244268408
-
-
for azepanes see, for example: c
-
for azepanes see, for example: c) A. R. Carrol, E. Hyde, J. Smith, R. J. Quinn, G. Guymer, P. I. Forster, J. Org. Chem. 2005, 70, 1096-1099;
-
(2005)
J. Org. Chem
, vol.70
, pp. 1096-1099
-
-
Carrol, A.R.1
Hyde, E.2
Smith, J.3
Quinn, R.J.4
Guymer, G.5
Forster, P.I.6
-
78
-
-
33646534197
-
-
d) M. C. De la Fuente, S. E. Pullan, I. Biesmans, D. Domínguez, J. Org. Chem. 2006, 71, 3963-3966;
-
(2006)
J. Org. Chem
, vol.71
, pp. 3963-3966
-
-
De la Fuente, M.C.1
Pullan, S.E.2
Biesmans, I.3
Domínguez, D.4
-
79
-
-
13144257750
-
-
for thiepanes see, for example
-
e) H. Li, Y. Blériot, J.-M. Mallet, E. Rodriguez-Garcia, P. Vogel, Y. Zhang, P. Sinaÿ, Tetrahedron: Asymmetry 2005, 16, 313-319; for thiepanes see, for example:
-
(2005)
Tetrahedron: Asymmetry
, vol.16
, pp. 313-319
-
-
Li, H.1
Blériot, Y.2
Mallet, J.-M.3
Rodriguez-Garcia, E.4
Vogel, P.5
Zhang, Y.6
Sinaÿ, P.7
-
80
-
-
30344445979
-
-
f) S. Dubaele, W. Jahnke, J. Schoepfer, J. Fuchs, P. Chène, Bioorg. Med. Chem. Lett. 2006, 16, 923-927;
-
(2006)
Bioorg. Med. Chem. Lett
, vol.16
, pp. 923-927
-
-
Dubaele, S.1
Jahnke, W.2
Schoepfer, J.3
Fuchs, J.4
Chène, P.5
-
81
-
-
24944565175
-
-
g) S. J. Tremont, L. F. Lee, H.-C. Huang, B. T. Keller, S. C. Banerjee, S. R. Both, A. J. Carpenter, C.-C. Wang, D. J. Garland, W. Huang, C. Jones, K. J. Koeller, S. A. Kolodziej, J. Li, R. E. Manning, M. W. Mahoney, R. E. Miller, D. A. Mischke, N. P. Rath, T. Fletcher, E.J. Reinhard, M.B. Tollefson, W. F. Vernier, G. M. Wagner, S. R. Rapp, J. Beaudry, K. Glenn, K. Regina, J. R. Schuh, M. E. Smith, J. S. Trivedi, D. B. Reitz, J. Med. Chem. 2005, 48, 5837-5852;
-
(2005)
J. Med. Chem
, vol.48
, pp. 5837-5852
-
-
Tremont, S.J.1
Lee, L.F.2
Huang, H.-C.3
Keller, B.T.4
Banerjee, S.C.5
Both, S.R.6
Carpenter, A.J.7
Wang, C.-C.8
Garland, D.J.9
Huang, W.10
Jones, C.11
Koeller, K.J.12
Kolodziej, S.A.13
Li, J.14
Manning, R.E.15
Mahoney, M.W.16
Miller, R.E.17
Mischke, D.A.18
Rath, N.P.19
Fletcher, T.20
Reinhard, E.J.21
Tollefson, M.B.22
Vernier, W.F.23
Wagner, G.M.24
Rapp, S.R.25
Beaudry, J.26
Glenn, K.27
Regina, K.28
Schuh, J.R.29
Smith, M.E.30
Trivedi, J.S.31
Reitz, D.B.32
more..
-
82
-
-
24744470290
-
-
h) H.-C. Huang, S. J. Tremont, L. F. Lee B. T. Keller, A. J. Carpenter, C.-C. Wang, S. C. Banerjee, S. R. Both, T. Fletcher, D. J. Garland, W. Huang, C. Jones, K. J. Koeller, S. A. Kolodziej, J. Li, R. E. Manning, M. W. Mahoney, R. E. Miller, D. A. Mischke, N. P. Rath, E. J. Reinhard, M. B. Tollefson, W. F. Vernier, G. M. Wagner, S. R. Rapp, J. Beaudry, K. Glenn, K. Regina, J. R. Schuh, M. E. Smith, J. S. Trivedi, D. B. Reitz, J. Med. Chem. 2005, 48, 5853-5868.
-
(2005)
J. Med. Chem
, vol.48
, pp. 5853-5868
-
-
Huang, H.-C.1
Tremont, S.J.2
Lee, L.F.3
Keller, B.T.4
Carpenter, A.J.5
Wang, C.-C.6
Banerjee, S.C.7
Both, S.R.8
Fletcher, T.9
Garland, D.J.10
Huang, W.11
Jones, C.12
Koeller, K.J.13
Kolodziej, S.A.14
Li, J.15
Manning, R.E.16
Mahoney, M.W.17
Miller, R.E.18
Mischke, D.A.19
Rath, N.P.20
Reinhard, E.J.21
Tollefson, M.B.22
Vernier, W.F.23
Wagner, G.M.24
Rapp, S.R.25
Beaudry, J.26
Glenn, K.27
Regina, K.28
Schuh, J.R.29
Smith, M.E.30
Trivedi, J.S.31
Reitz, D.B.32
more..
-
83
-
-
53849148854
-
-
For an overview of the previously developed synthetic approaches to heterocyclic seven-membered rings see references [2-17] cited in reference [30] of the present article
-
For an overview of the previously developed synthetic approaches to heterocyclic seven-membered rings see references [2-17] cited in reference [30] of the present article.
-
-
-
-
84
-
-
33750327789
-
-
A part of these results has been reported in a preliminary communication: Y. Coquerel, D. Bensa, A. Doutheau, J. Rodriguez, Org. Lett. 2006, 8, 4819-4822.
-
A part of these results has been reported in a preliminary communication: Y. Coquerel, D. Bensa, A. Doutheau, J. Rodriguez, Org. Lett. 2006, 8, 4819-4822.
-
-
-
-
86
-
-
0001060227
-
-
a) M. P. Moyer, P. L. Feldman, H. Rapoport, J. Org. Chem. 1985, 50, 5223-5230;
-
(1985)
J. Org. Chem
, vol.50
, pp. 5223-5230
-
-
Moyer, M.P.1
Feldman, P.L.2
Rapoport, H.3
-
87
-
-
0030914314
-
-
b) M. A. Calter, P. M. Sugathapala, C. Zhu, Tetrahedron Lett. 1997, 38, 3837-3840;
-
(1997)
Tetrahedron Lett
, vol.38
, pp. 3837-3840
-
-
Calter, M.A.1
Sugathapala, P.M.2
Zhu, C.3
-
89
-
-
0343953365
-
-
F. Lacrampe, F. Léost, A. Doutheau, Tetrahedron Lea. 2000, 41, 4773-4776.
-
(2000)
Tetrahedron Lea
, vol.41
, pp. 4773-4776
-
-
Lacrampe, F.1
Léost, F.2
Doutheau, A.3
-
90
-
-
0028871262
-
-
This behaviour has previously been reported when no aldolisation was allowed after the Michael addition: M.-H. Filippini, J. Rodriguez, Synth. Commun. 1995, 25, 245-252
-
This behaviour has previously been reported when no aldolisation was allowed after the Michael addition: M.-H. Filippini, J. Rodriguez, Synth. Commun. 1995, 25, 245-252.
-
-
-
|