-
3
-
-
0001720136
-
-
R. S. Cahn, C. K. Ingold, V. Prelog, Angew. Chem. 1966, 78, 413;
-
(1966)
Angew. Chem.
, vol.78
, pp. 413
-
-
Cahn, R.S.1
Ingold, C.K.2
Prelog, V.3
-
7
-
-
0000293403
-
-
b) A. C. Cope, K. Banholzer, H. Keller, B. A. Pawson, J. J. Wang, H. J. S. Winkler, J. Am. Chem. Soc. 1965, 87, 3644;
-
(1965)
J. Am. Chem. Soc.
, vol.87
, pp. 3644
-
-
Cope, A.C.1
Banholzer, K.2
Keller, H.3
Pawson, B.A.4
Wang, J.J.5
Winkler, H.J.S.6
-
9
-
-
0033515477
-
-
d) D. M. Pawar, S. D. Miggins, S. V. Smith, E. A. Noe, J. Org. Chem. 1999, 64, 2418.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 2418
-
-
Pawar, D.M.1
Miggins, S.D.2
Smith, S.V.3
Noe, E.A.4
-
12
-
-
0034708730
-
-
b) A. Sudau, W. Münch, J. W. Bats, U. Nubbemeyer, J. Org. Chem. 2000, 65, 1710.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 1710
-
-
Sudau, A.1
Münch, W.2
Bats, J.W.3
Nubbemeyer, U.4
-
13
-
-
0001080877
-
-
For further syntheses of unsaturated medium-sized ring lactams including some transannular reactions see: a) C. J. Deur , M. W. Miller, L. S. Hegedus, J. Org. Chem. 1996, 61, 2871;
-
(1996)
J. Org. Chem.
, vol.61
, pp. 2871
-
-
Deur, C.J.1
Miller, M.W.2
Hegedus, L.S.3
-
14
-
-
0002192429
-
-
b) P. A. Evans, A. B. Holmes, R. P. McGeary, A. Nadin, K. Russell, P. J. O'Hanlon, N. D. Pearson, J. Chem. Soc. Perkin Trans. 1 1996, 123;
-
(1996)
J. Chem. Soc. Perkin Trans. 1
, pp. 123
-
-
Evans, P.A.1
Holmes, A.B.2
McGeary, R.P.3
Nadin, A.4
Russell, K.5
O'Hanlon, P.J.6
Pearson, N.D.7
-
15
-
-
0028789512
-
-
c) P. A. Evans, A. B. Holmes, I. Collins, P. R. Raithby, K. Russell, J. Chem. Soc. Chem. Commun. 1995, 2325;
-
(1995)
J. Chem. Soc. Chem. Commun.
, pp. 2325
-
-
Evans, P.A.1
Holmes, A.B.2
Collins, I.3
Raithby, P.R.4
Russell, K.5
-
16
-
-
0026497760
-
-
d) P. A. Evans, A. B. Holmes, K. Russell, Tetrahedron Lett. 1992, 33, 6857;
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 6857
-
-
Evans, P.A.1
Holmes, A.B.2
Russell, K.3
-
17
-
-
0026492646
-
-
e) P. A. Evans, I. Collins, P. Hamley, A. B. Holmes, P. R. Raithby, K. Russell, Tetrahedron Lett. 1992, 33, 6859;
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 6859
-
-
Evans, P.A.1
Collins, I.2
Hamley, P.3
Holmes, A.B.4
Raithby, P.R.5
Russell, K.6
-
21
-
-
0006084872
-
-
note
-
Ratio of 3:4 after heating to 60°C: 3a:4a = 5:95 (4 h), 3b:4b = 1:13 (3 h), 3c:4c = 1:4.3 (3 h). Separation of 3 and 4 by column chromatography or HPLC, if necessary. In some experiments starting from pR-4, some pS-3 reamined as impurity. Usually, the reactant ratio (pS-3/pR-4) was completely transferred on generating the corresponding products (no epimerization).
-
-
-
-
22
-
-
0025305030
-
-
Conformational flexibility of azonanones: a) G. L. Olson, M. E. Voss, D. E. Hill, M. Kahn, V. S. Madison, C. M. Cook, J. Am. Chem. Soc. 1990, 112, 323;
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 323
-
-
Olson, G.L.1
Voss, M.E.2
Hill, D.E.3
Kahn, M.4
Madison, V.S.5
Cook, C.M.6
-
23
-
-
84987487359
-
-
b) Terpenes: G. Guella, G. Chiasera, I. D'Diaye, F. Pietra, Helv. Chim. Acta 1994, 77, 1203;
-
(1994)
Helv. Chim. Acta
, vol.77
, pp. 1203
-
-
Guella, G.1
Chiasera, G.2
D'Diaye, I.3
Pietra, F.4
-
24
-
-
0000162171
-
-
c) A. J. Minnaard, J. B. P. A. Wijnberg, A. de Groot, J. Org. Chem. 1997, 62, 7346;
-
(1997)
J. Org. Chem.
, vol.62
, pp. 7346
-
-
Minnaard, A.J.1
Wijnberg, J.B.P.A.2
De Groot, A.3
-
26
-
-
49649141705
-
-
a) U. Mende, B. Radüchel, W. Skuballa, H. Vorbr̈ggen, Tetrahedron Lett. 1975, 629;
-
(1975)
Tetrahedron Lett.
, pp. 629
-
-
Mende, U.1
Radüchel, B.2
Skuballa, W.3
Vorbr̈ggen, H.4
-
29
-
-
0019845784
-
-
Preparation of diazomethane: D. A. Evans, S. P. Tanis, D. J. Hart, J. Am. Chem. Soc. 1981, 103, 5813.
-
(1981)
J. Am. Chem. Soc.
, vol.103
, pp. 5813
-
-
Evans, D.A.1
Tanis, S.P.2
Hart, D.J.3
-
31
-
-
0037782375
-
-
b) M. J. Södergren, D. A. Alonso, A. V. Bedekar, P. G. Andersson, Tetrahedron Lett. 1997, 38, 6897; for a modified preparation procedure of the reagent see the Supporting Information.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 6897
-
-
Södergren, M.J.1
Alonso, D.A.2
Bedekar, A.V.3
Andersson, P.G.4
-
32
-
-
33751499952
-
-
a) D. A. Evans, M. M. Faul, M. T. Bilodeau, J. Org. Chem. 1991, 56, 6744;
-
(1991)
J. Org. Chem.
, vol.56
, pp. 6744
-
-
Evans, D.A.1
Faul, M.M.2
Bilodeau, M.T.3
-
33
-
-
11644312278
-
-
b) D. A. Evans, M. M. Faul, M. T. Bilodeau, J. Am. Chem. Soc. 1994, 116, 2742;
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 2742
-
-
Evans, D.A.1
Faul, M.M.2
Bilodeau, M.T.3
-
34
-
-
0007448978
-
-
c) Z. Li, K. R. Conser, E. N. Jacobsen, J. Am. Chem. Soc. 1993, 115, 5326.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 5326
-
-
Li, Z.1
Conser, K.R.2
Jacobsen, E.N.3
-
35
-
-
33847583868
-
-
For spectral data of γ-butyrolactam 23, see the Supporting Information
-
For spectral data of γ-butyrolactam 23, see the Supporting Information.
-
-
-
-
38
-
-
33744770809
-
-
a) T. K. M. Shing, E. K. W. Tam, V. W.-F. Tai, I. H. F. Chung, Q. Jiang, Chem. Eur. J. 1996, 2, 50;
-
(1996)
Chem. Eur. J.
, vol.2
, pp. 50
-
-
Shing, T.K.M.1
Tam, E.K.W.2
Tai, V.W.-F.3
Chung, I.H.F.4
Jiang, Q.5
-
39
-
-
0001409623
-
-
b) T. K. M. Shing, V. W.-F. Tai, E. K. W. Tam, Angew. Chem. 1994, 106, 2408;
-
(1994)
Angew. Chem.
, vol.106
, pp. 2408
-
-
Shing, T.K.M.1
Tai, V.W.-F.2
Tam, E.K.W.3
-
43
-
-
0000733886
-
-
G. Höfle, W. Steglich, H. Vorbrüggen, Angew. Chem. 1978, 90, 602;
-
(1978)
Angew. Chem.
, vol.90
, pp. 602
-
-
Höfle, G.1
Steglich, W.2
Vorbrüggen, H.3
-
46
-
-
33847592142
-
-
For detailed NOE data see the Supporting Information
-
For detailed NOE data see the Supporting Information.
-
-
-
-
47
-
-
0006084873
-
-
note
-
1 (Figure 3).
-
-
-
-
48
-
-
0000048225
-
-
a) S. E. Denmark, P. A. Barsanti, K.-T. Wong, R. A. Stavenger, J. Org. Chem. 1998, 63, 2428;
-
(1998)
J. Org. Chem.
, vol.63
, pp. 2428
-
-
Denmark, S.E.1
Barsanti, P.A.2
Wong, K.-T.3
Stavenger, R.A.4
-
50
-
-
33847594728
-
-
For spectral data of γ-butyrolactones 22 see the Supporting Information
-
For spectral data of γ-butyrolactones 22 see the Supporting Information.
-
-
-
-
51
-
-
0006073008
-
-
note
-
Generally, the lactones 22 can be used as intermediates to generate the desired indolizidinones 19; after hydrogenolytic removal of the benzylamine, a subsequent lactone-lactam conversion should lead to the desired bicyclic products.
-
-
-
-
55
-
-
0006119582
-
-
note
-
1 (Figure 4).
-
-
-
-
56
-
-
0006114404
-
-
note
-
As a matter of principle, the lactam function can adopt four discrete arrangements: 2 x Z (pR and pS) and 2 x E (pR and pS) with respect to the oxygen and benzyl groups.
-
-
-
-
58
-
-
0001178865
-
-
and A. Deiters, C. Mück-Lichtenfeld, R. Fröhlich, D. Hoppe, Org. Lett. 2000, 2, 2415 (including kinetic measurements); force-field MM+ calculations had been carried out with Hyperchem by arranging C3 and C9 in a cis configuration with respect to the double-bond character of the lactam unit. Structures 11 and minor-11 as outlined in Scheme 5, data are given in Table 4. Potential trans-11 with C3 and C9 trans with respect to the double bond character of the lactam unit not shown.
-
(2000)
Org. Lett.
, vol.2
, pp. 2415
-
-
Deiters, A.1
Mück-Lichtenfeld, C.2
Fröhlich, R.3
Hoppe, D.4
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