-
1
-
-
47149086171
-
-
Schnute M E., Brideau R J., Collier S A., Cudahy M M., Hopkins T A., Knechtel M L., Oien N L., Sackett R S., Scott A, Stephan M L., Wathen M W., Wieber J L., Bioorg. Med. Chem. Lett. 2008 18 3856
-
(2008)
Bioorg. Med. Chem. Lett.
, vol.18
, pp. 3856
-
-
Schnute, M.E.1
Brideau, R.J.2
Collier, S.A.3
Cudahy, M.M.4
Hopkins, T.A.5
Knechtel, M.L.6
Oien, N.L.7
Sackett, R.S.8
Scott, A.9
Stephan, M.L.10
Wathen, M.W.11
Wieber, J.L.12
-
2
-
-
33846185943
-
-
Brookings D, Davenport R J., Davis J, Galvin F C. A., Lloyd S, Mack S R., Owens R, Sabin V, Wynn J, Bioorg. Med. Chem. Lett. 2007 17 562
-
(2007)
Bioorg. Med. Chem. Lett.
, vol.17
, pp. 562
-
-
Brookings, D.1
Davenport, R.J.2
Davis, J.3
Galvin, F.C.A.4
Lloyd, S.5
MacK, S.R.6
Owens, R.7
Sabin, V.8
Wynn, J.9
-
3
-
-
5544272766
-
-
Blanchard J E., Elowe N H., Huitema C, Fortin P D., Cechetto J D., Eltis L D., Brown E D., Chem. Biol. 2004 11 1445
-
(2004)
Chem. Biol.
, vol.11
, pp. 1445
-
-
Blanchard, J.E.1
Elowe, N.H.2
Huitema, C.3
Fortin, P.D.4
Cechetto, J.D.5
Eltis, L.D.6
Brown, E.D.7
-
5
-
-
0033836836
-
-
Chang G.-J, Wu M.-H, Chen W.-P, Kuo S.-C, Su M.-J, Drug Dev. Res. 2000 50 170
-
(2000)
Drug Dev. Res.
, vol.50
, pp. 170
-
-
Chang, G.-J.1
Wu, M.-H.2
Chen, W.-P.3
Kuo, S.-C.4
Su, M.-J.5
-
6
-
-
0028921359
-
-
Huang A.-C, Lin T.-P, Kuo S.-C, Wang J.-P, J. Nat. Prod. 1995 58 117
-
(1995)
J. Nat. Prod.
, vol.58
, pp. 117
-
-
Huang, A.-C.1
Lin, T.-P.2
Kuo, S.-C.3
Wang, J.-P.4
-
8
-
-
0141630849
-
-
Bossharth E, Desbordes P, Monteiro N, Balme G, Org. Lett. 2003 5 2441
-
(2003)
Org. Lett.
, vol.5
, pp. 2441
-
-
Bossharth, E.1
Desbordes, P.2
Monteiro, N.3
Balme, G.4
-
9
-
-
33646453634
-
-
Aillaud I, Bossharth E, Conreaux D, Desbordes P, Monteiro N, Balme G, Org. Lett. 2006 8 1113
-
(2006)
Org. Lett.
, vol.8
, pp. 1113
-
-
Aillaud, I.1
Bossharth, E.2
Conreaux, D.3
Desbordes, P.4
Monteiro, N.5
Balme, G.6
-
10
-
-
57749092637
-
-
Bossharth E, Desbordes P, Monteiro N, Balme G, Tetrahedron Lett. 2009 50 614
-
(2009)
Tetrahedron Lett.
, vol.50
, pp. 614
-
-
Bossharth, E.1
Desbordes, P.2
Monteiro, N.3
Balme, G.4
-
11
-
-
55249093394
-
-
Conreaux D, Belot S, Desbordes P, Monteiro N, Balme G, J. Org. Chem. 2008 73 8619
-
(2008)
J. Org. Chem.
, vol.73
, pp. 8619
-
-
Conreaux, D.1
Belot, S.2
Desbordes, P.3
Monteiro, N.4
Balme, G.5
-
12
-
-
57749092637
-
-
Conreaux D, Delaunay T, Desbordes P, Monteiro N, Balme G, Tetrahedron Lett. 2009 50 614
-
(2009)
Tetrahedron Lett.
, vol.50
, pp. 614
-
-
Conreaux, D.1
Delaunay, T.2
Desbordes, P.3
Monteiro, N.4
Balme, G.5
-
13
-
-
33846581473
-
-
Conreaux D, Bossharth E, Monteiro N, Desbordes P, Vors J.-P, Balme G, Org. Lett. 2007 9 271
-
(2007)
Org. Lett.
, vol.9
, pp. 271
-
-
Conreaux, D.1
Bossharth, E.2
Monteiro, N.3
Desbordes, P.4
Vors, J.-P.5
Balme, G.6
-
14
-
-
0001116319
-
-
For mechanistic insights into acid-induced desilylations of silylacetylenes, see
-
For mechanistic insights into acid-induced desilylations of silylacetylenes, see:, Siehl H.-U, Kaufmann F.-P, Hori K, J. Am. Chem. Soc. 1992 114 9343
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 9343
-
-
Siehl, H.-U.1
Kaufmann, F.-P.2
Hori, K.3
-
15
-
-
0035962679
-
-
For a previous synthesis of this compound see
-
For a previous synthesis of this compound see:, Bar G, Parsons A F., Thomas C B., Tetrahedron 2001 57 4719
-
(2001)
Tetrahedron
, vol.57
, pp. 4719
-
-
Bar, G.1
Parsons, A.F.2
Thomas, C.B.3
-
16
-
-
0017405222
-
-
It is likely that, due to steric congestion, the methoxy methyl group in 2a is rotated out of the plane of the pyridinone ring resulting in decreased stability to nucleophilic attack with respect to 1a. This effect has often been invoked to explain the high degree of selectivity observed in the cleavage of polymethoxyarenes and is also expected to affect the rate of demethylation of benzo-fused 4-methoxypyridin-2-ones (quinolin-2-ones) like 3a. For leading references, see
-
It is likely that, due to steric congestion, the methoxy methyl group in 2a is rotated out of the plane of the pyridinone ring resulting in decreased stability to nucleophilic attack with respect to 1a. This effect has often been invoked to explain the high degree of selectivity observed in the cleavage of polymethoxyarenes and is also expected to affect the rate of demethylation of benzo-fused 4-methoxypyridin-2-ones (quinolin-2-ones) like 3a. For leading references, see:, Ahmad R, Saá J M., Cava M P., J. Org. Chem. 1977 42 1228
-
(1977)
J. Org. Chem.
, vol.42
, pp. 1228
-
-
Ahmad, R.1
Saá, J.M.2
Cava, M.P.3
-
17
-
-
0001202054
-
-
Jardon P W., Vickery E H., Pahler L F., Pourahmady N, Mains G J., Eisenbraun E J., J. Org. Chem. 1984 49 2130
-
(1984)
J. Org. Chem.
, vol.49
, pp. 2130
-
-
Jardon, P.W.1
Vickery, E.H.2
Pahler, L.F.3
Pourahmady, N.4
Mains, G.J.5
Eisenbraun, E.J.6
|