-
1
-
-
59449101761
-
-
Blunt, J. W.; Copp, B. R.; Hu, W.-P.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. Nat. Prod. Rep. 2009, 26, 170-244
-
(2009)
Nat. Prod. Rep.
, vol.26
, pp. 170-244
-
-
Blunt, J.W.1
Copp, B.R.2
Hu, W.-P.3
Munro, M.H.G.4
Northcote, P.T.5
Prinsep, M.R.6
-
2
-
-
67650651992
-
-
Jackson, K. L.; Henderson, J. A.; Phillips, A. J. Chem. Rev. 2009, 109, 3044-3079
-
(2009)
Chem. Rev.
, vol.109
, pp. 3044-3079
-
-
Jackson, K.L.1
Henderson, J.A.2
Phillips, A.J.3
-
6
-
-
9644257336
-
-
Řezanka, T.; Hanuš, L. O.; Dembitsky, V. M. Tetrahedron 2004, 60, 12191-12199
-
(2004)
Tetrahedron
, vol.60
, pp. 12191-12199
-
-
Řezanka, T.1
Hanuš, L.O.2
Dembitsky, V.M.3
-
7
-
-
0035905526
-
-
Abraham, L.; Czerwonka, R.; Hiersemann, M. Angew. Chem., Int. Ed. 2001, 40, 4700-4703
-
(2001)
Angew. Chem., Int. Ed.
, vol.40
, pp. 4700-4703
-
-
Abraham, L.1
Czerwonka, R.2
Hiersemann, M.3
-
8
-
-
7044286189
-
-
Abraham, L.; Körner, M.; Schwab, P.; Hiersemann, M. Adv. Synth. Catal. 2004, 346, 1281-1294
-
(2004)
Adv. Synth. Catal.
, vol.346
, pp. 1281-1294
-
-
Abraham, L.1
Körner, M.2
Schwab, P.3
Hiersemann, M.4
-
9
-
-
78449269001
-
-
Compound 4 has been prepared on 20 g scale in five steps from commercial 2-butyn-1-ol according to the published procedure; see
-
Compound 4 has been prepared on 20 g scale in five steps from commercial 2-butyn-1-ol according to the published procedure; see
-
-
-
-
10
-
-
64349087921
-
-
The synthesis requires access to preparative HPLC for the separation of vinyl ether double bond isomers
-
Rehbein, J.; Leick, S.; Hiersemann, M. J. Org. Chem. 2009, 74, 1531-1540 The synthesis requires access to preparative HPLC for the separation of vinyl ether double bond isomers.
-
(2009)
J. Org. Chem.
, vol.74
, pp. 1531-1540
-
-
Rehbein, J.1
Leick, S.2
Hiersemann, M.3
-
11
-
-
0033603853
-
-
Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559-7573
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 7559-7573
-
-
Evans, D.A.1
Miller, S.J.2
Lectka, T.3
Von Matt, P.4
-
12
-
-
78449303283
-
-
For selected applications of the catalytic asymmetric Gosteli-Claisen rearrangement in natural product synthesis, see
-
For selected applications of the catalytic asymmetric Gosteli-Claisen rearrangement in natural product synthesis, see
-
-
-
-
15
-
-
33845282886
-
-
Reduction in the presence of (R)- 7 provided (2 S)- 8 in 87% (dr = 93:7). Treatment with K-Selectride also delivered (2 S)- 8 (81%, dr = 85:15), albeit with limited scalability (1 g). Far inferior yields (60%) and diastereoselectivities (dr = 4:1) were obtained with (S)- 7
-
Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553 Reduction in the presence of (R)- 7 provided (2 S)- 8 in 87% (dr = 93:7). Treatment with K-Selectride also delivered (2 S)- 8 (81%, dr = 85:15), albeit with limited scalability (1 g). Far inferior yields (60%) and diastereoselectivities (dr = 4:1) were obtained with (S)- 7
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 5551-5553
-
-
Corey, E.J.1
Bakshi, R.K.2
Shibata, S.3
-
18
-
-
0000605995
-
-
Nystrom, R. F.; Chaikin, S. W.; Brown, W. G. J. Am. Chem. Soc. 1949, 71, 3245-3246
-
(1949)
J. Am. Chem. Soc.
, vol.71
, pp. 3245-3246
-
-
Nystrom, R.F.1
Chaikin, S.W.2
Brown, W.G.3
-
19
-
-
0000876386
-
-
Oikawa, Y.; Nishi, T.; Yonemitsu, O. Tetrahedron Lett. 1983, 24, 4037-4040
-
(1983)
Tetrahedron Lett.
, vol.24
, pp. 4037-4040
-
-
Oikawa, Y.1
Nishi, T.2
Yonemitsu, O.3
-
21
-
-
0012016624
-
-
Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129
-
(1981)
J. Am. Chem. Soc.
, vol.103
, pp. 2127-2129
-
-
Evans, D.A.1
Bartroli, J.2
Shih, T.L.3
-
22
-
-
0000902240
-
-
Ewing, W. R.; Bhat, K. L.; Joullie, M. M. Tetrahedron 1986, 42, 5863-5868
-
(1986)
Tetrahedron
, vol.42
, pp. 5863-5868
-
-
Ewing, W.R.1
Bhat, K.L.2
Joullie, M.M.3
-
23
-
-
0032508077
-
-
Shimano, M.; Shibata, T.; Kamei, N. Tetrahedron Lett. 1998, 39, 4363-4366
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 4363-4366
-
-
Shimano, M.1
Shibata, T.2
Kamei, N.3
-
24
-
-
0000776391
-
-
Corey, E. J.; Cho, H.; Rücker, C.; Hua, D. H. Tetrahedron Lett. 1981, 22, 3455-3458
-
(1981)
Tetrahedron Lett.
, vol.22
, pp. 3455-3458
-
-
Corey, E.J.1
Cho, H.2
Rücker, C.3
Hua, D.H.4
-
25
-
-
33845375340
-
-
Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. J. Am. Chem. Soc. 1986, 108, 6395-6397
-
(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 6395-6397
-
-
Evans, D.A.1
Britton, T.C.2
Dorow, R.L.3
Dellaria, J.F.4
-
26
-
-
0025036353
-
-
Fürstner, A.; Koglbauer, U.; Weidmann, H. J. Carbohydr. Chem. 1990, 9, 561-570
-
(1990)
J. Carbohydr. Chem.
, vol.9
, pp. 561-570
-
-
Fürstner, A.1
Koglbauer, U.2
Weidmann, H.3
-
29
-
-
78449273058
-
-
Jäger, V. Synthesis 2000, 7, 1027-1033
-
(2000)
Synthesis
, vol.7
, pp. 1027-1033
-
-
Jäger, V.1
-
32
-
-
33947465724
-
-
Miller, A. E. G.; Biss, J. W.; Schwartzman, L. H. J. Org. Chem. 1959, 24, 627-630
-
(1959)
J. Org. Chem.
, vol.24
, pp. 627-630
-
-
Miller, A.E.G.1
Biss, J.W.2
Schwartzman, L.H.3
-
33
-
-
78449287388
-
-
Prepared in four steps from 11; see
-
Prepared in four steps from 11; see
-
-
-
-
34
-
-
0029827812
-
-
Lin, N.-H.; Overman, L. E.; Rabinowitz, M. H.; Robinson, L. A.; Sharp, M. J.; Zablocki, J. J. Am. Chem. Soc. 1996, 118, 9062-9072
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 9062-9072
-
-
Lin, N.-H.1
Overman, L.E.2
Rabinowitz, M.H.3
Robinson, L.A.4
Sharp, M.J.5
Zablocki, J.6
-
36
-
-
0023885132
-
-
Evans, D. A.; Bender, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 110, 2506-2526
-
(1988)
J. Am. Chem. Soc.
, vol.110
, pp. 2506-2526
-
-
Evans, D.A.1
Bender, S.L.2
Morris, J.3
-
37
-
-
0000786664
-
-
Experimental details are provided in the Supporting Information
-
Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1988, 44, 1299-1304 Experimental details are provided in the Supporting Information.
-
(1988)
Tetrahedron
, vol.44
, pp. 1299-1304
-
-
Gramatica, P.1
Manitto, P.2
Monti, D.3
Speranza, G.4
-
38
-
-
0030592760
-
-
Keyling-Bilger, F.; Schmitt, G.; Beck, A.; Luu, B. Tetrahedron 1996, 52, 14891-14904
-
(1996)
Tetrahedron
, vol.52
, pp. 14891-14904
-
-
Keyling-Bilger, F.1
Schmitt, G.2
Beck, A.3
Luu, B.4
-
44
-
-
0018354285
-
-
Fukuyama, T.; Wang, C.-L. J.; Kishi, Y. J. Am. Chem. Soc. 1979, 101, 260-262
-
(1979)
J. Am. Chem. Soc.
, vol.101
, pp. 260-262
-
-
Fukuyama, T.1
Wang, C.-L.J.2
Kishi, Y.3
-
46
-
-
77950221191
-
-
Xiong, Z.; Busch, R.; Corey, E. J. Org. Lett. 2010, 12, 1512-1514
-
(2010)
Org. Lett.
, vol.12
, pp. 1512-1514
-
-
Xiong, Z.1
Busch, R.2
Corey, E.J.3
-
47
-
-
33748645648
-
-
Tanimoto, N.; Gerritz, S. W.; Sawabe, A.; Noda, T.; Filla, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 673-675
-
(1994)
Angew. Chem., Int. Ed. Engl.
, vol.33
, pp. 673-675
-
-
Tanimoto, N.1
Gerritz, S.W.2
Sawabe, A.3
Noda, T.4
Filla, S.A.5
Masamune, S.6
-
51
-
-
0345491105
-
-
Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
-
(1988)
Phys. Rev. B
, vol.37
, pp. 785-789
-
-
Lee, C.1
Yang, W.2
Parr, R.G.3
-
52
-
-
78449292273
-
-
The calculations were carried out with Gaussian03, see:.; Gaussian, Inc.: Wallingford, CT,. Full reference given in the Supporting Information
-
The calculations were carried out with Gaussian03, see: Frisch, M. J. Gaussian 03, revision E.01; Gaussian, Inc.: Wallingford, CT, 2004. Full reference given in the Supporting Information.
-
(2004)
Gaussian 03, Revision E.01
-
-
Frisch, M.J.1
-
53
-
-
78449295865
-
-
Single-point self-consistent reaction field (SCRF) calculations using the PCM solvation model as implemented in Gaussian 03 (PCM, solvent = acetone) at the PCM//B3LYP/6-311++G(d,p) level support this notion and predict a free energy difference of 4.0 kcal/mol in favor of II
-
Single-point self-consistent reaction field (SCRF) calculations using the PCM solvation model as implemented in Gaussian 03 (PCM, solvent = acetone) at the PCM//B3LYP/6-311++G(d,p) level support this notion and predict a free energy difference of 4.0 kcal/mol in favor of II.
-
-
-
-
54
-
-
1642334165
-
-
Shiina, I.; Kubota, M.; Oshiumi, H.; Hashizume, M. J. Org. Chem. 2004, 69, 1822-1830
-
(2004)
J. Org. Chem.
, vol.69
, pp. 1822-1830
-
-
Shiina, I.1
Kubota, M.2
Oshiumi, H.3
Hashizume, M.4
-
55
-
-
0033598258
-
-
Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956
-
(1999)
Org. Lett.
, vol.1
, pp. 953-956
-
-
Scholl, M.1
Ding, S.2
Lee, C.W.3
Grubbs, R.H.4
-
56
-
-
78449311148
-
-
3 J coupling constant of the vinylic protons of 23 (16.1 Hz) is in good accordanced with reported value for the natural product (15.2 Hz)
-
3 J coupling constant of the vinylic protons of 23 (16.1 Hz) is in good accordanced with reported value for the natural product (15.2 Hz).
-
-
-
-
57
-
-
78449299837
-
-
4F in MeOH, see
-
4F in MeOH, see
-
-
-
-
59
-
-
78449289335
-
-
2OH, were not successful
-
2OH, were not successful.
-
-
-
|