-
1
-
-
0033998334
-
-
T. M. Willson, P. J. Brown, D. D. Sternbach, B. R. Henke, J. Med. Chem. 2000, 43, 527-550.
-
(2000)
J. Med. Chem.
, vol.43
, pp. 527-550
-
-
Willson, T.M.1
Brown, P.J.2
Sternbach, D.D.3
Henke, B.R.4
-
2
-
-
0028972025
-
-
a) B. M. Forman, P. Tontonoz, J. Chen, R. P. Brun, B. M. Spielgelman, R. M. Evans, Cell 1995, 83, 803-812;
-
(1995)
Cell
, vol.83
, pp. 803-812
-
-
Forman, B.M.1
Tontonoz, P.2
Chen, J.3
Brun, R.P.4
Spielgelman, B.M.5
Evans, R.M.6
-
3
-
-
0028972026
-
-
b) S. A. Kliewer, J. M. Lenhard, T. M. Wilson, I. Patel, D. C. Morris, J. M. Lehmann, Cell 1995, 83, 813-819.
-
(1995)
Cell
, vol.83
, pp. 813-819
-
-
Kliewer, S.A.1
Lenhard, J.M.2
Wilson, T.M.3
Patel, I.4
Morris, D.C.5
Lehmann, J.M.6
-
4
-
-
0001523417
-
-
a) G. Piancatelli, A. Scettri, S. Barbadoro, Tetrahedron Lett. 1976, 17, 3555-3558;
-
(1976)
Tetrahedron Lett.
, vol.17
, pp. 3555-3558
-
-
Piancatelli, G.1
Scettri, A.2
Barbadoro, S.3
-
5
-
-
49349131844
-
-
b) G. Piancatelli, A. Scettri, G. David, M. D'Auria, Tetrahedron 1978, 34, 2775-2778;
-
(1978)
Tetrahedron
, vol.34
, pp. 2775-2778
-
-
Piancatelli, G.1
Scettri, A.2
David, G.3
D'Auria, M.4
-
8
-
-
0041918113
-
-
Under persistent acid treatment or, most conveniently, upon reaction with base, the most stable 2-substituted-4-hydroxycyclopent-2-en-1-one isomers are isolated instead. The utility of the synthetic sequence going from furfurylcarbinols (themselves the addition products of Grignard reagents to furfural) to 2-alkyl-4-hydroxycyclopent-2-en-1-ones has been recognized in the prostaglandin field and constitutes the key step in the synthesis of PGA derivatives. A. Rodríguez, M. Nomen, B. W. Spur, J. Godfroid, Eur. J. Org. Chem. 1999, 2655-2662.
-
(1999)
Eur. J. Org. Chem.
, pp. 2655-2662
-
-
Rodríguez, A.1
Nomen, M.2
Spur, B.W.3
Godfroid, J.4
-
9
-
-
0000703627
-
-
R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797-853; Angew. Chem. Int. Ed. Engl. 1969, 8, 781-853.
-
(1969)
Angew. Chem.
, vol.81
, pp. 797-853
-
-
Woodward, R.B.1
Hoffmann, R.2
-
10
-
-
84981778017
-
-
R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797-853; Angew. Chem. Int. Ed. Engl. 1969, 8, 781-853.
-
(1969)
Angew. Chem. Int. Ed. Engl.
, vol.8
, pp. 781-853
-
-
-
11
-
-
0343196689
-
-
a) A. R. de Lera, J. García Rey, D. A. Hrovat, B. Iglesias, S. López, Tetrahedron Lett. 1997, 38, 7425-7428;
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 7425-7428
-
-
De Lera, A.R.1
García Rey, J.2
Hrovat, D.A.3
Iglesias, B.4
López, S.5
-
12
-
-
0034602087
-
-
b) B. Iglesias, A. R. de Lera, J. Rodríguez-Otero, S. López, Chem. Eur. J. 2000, 6, 4021-4033.
-
(2000)
Chem. Eur. J.
, vol.6
, pp. 4021-4033
-
-
Iglesias, B.1
De Lera, A.R.2
Rodríguez-Otero, J.3
López, S.4
-
13
-
-
0000646877
-
Nazarov and related cationic cyclizations
-
(Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford
-
For reviews, see: a) S. E. Denmark, Nazarov and Related Cationic Cyclizations, in Comprehensive Organic Synthesis, Vol. 5, (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, pp. 751-784;
-
(1991)
Comprehensive Organic Synthesis
, vol.5
, pp. 751-784
-
-
Denmark, S.E.1
-
14
-
-
0001992172
-
The Nazarov cyclization
-
(Ed.: L. A. Paquette), Wiley, New York
-
b) K. L. Habermas, S. E. Denmark, T. K. Jones, The Nazarov Cyclization, in Organic Reactions, vol. 45, (Ed.: L. A. Paquette), Wiley, New York, 1994, pp. 1-158.
-
(1994)
Organic Reactions
, vol.45
, pp. 1-158
-
-
Habermas, K.L.1
Denmark, S.E.2
Jones, T.K.3
-
15
-
-
0345520231
-
-
The scope of the Nazarov reaction for synthesis of cyclopentenoids has recently been expanded by interception of the oxyallylcation by hydrides (8 a-c), or by olefins and aryl rings in cascade reactions (8 d-f). a) Interrupted Nazarov: J. A. Bender, A. E. Blize, C. C. Browder, S. Giese, F. G. West, J. Org. Chem. 1998, 63, 2430-2431;
-
(1998)
J. Org. Chem.
, vol.63
, pp. 2430-2431
-
-
Bender, J.A.1
Blize, A.E.2
Browder, C.C.3
Giese, S.4
West, F.G.5
-
16
-
-
0000085486
-
-
b) A. Pawda, T. M. Heidelbaugh, J. T. Kuether, M. S. McClure, J. Org. Chem. 1998, 63, 6778-6779;
-
(1998)
J. Org. Chem.
, vol.63
, pp. 6778-6779
-
-
Pawda, A.1
Heidelbaugh, T.M.2
Kuether, J.T.3
McClure, M.S.4
-
18
-
-
0033518564
-
-
d) Trapping of the oxyallyl intermediate: Y. Wang, A. M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 876-877;
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 876-877
-
-
Wang, Y.1
Arif, A.M.2
West, F.G.3
-
19
-
-
0033581158
-
-
e) J. A. Bender, A. M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 7443-7444;
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 7443-7444
-
-
Bender, J.A.1
Arif, A.M.2
West, F.G.3
-
20
-
-
0035922380
-
-
f) C. C. Browder, F. P. Marmsätter, F. G. West, Org. Lett. 2001, 3, 3033-3035;
-
(2001)
Org. Lett.
, vol.3
, pp. 3033-3035
-
-
Browder, C.C.1
Marmsätter, F.P.2
West, F.G.3
-
21
-
-
0141855021
-
-
g) Y. Wang, B. D. Schill, A. M. Arif, F. G. West, Org. Lett. 2003, 5, 2747-2750.
-
(2003)
Org. Lett.
, vol.5
, pp. 2747-2750
-
-
Wang, Y.1
Schill, B.D.2
Arif, A.M.3
West, F.G.4
-
23
-
-
0022535582
-
-
b) M. A. Tius, D. P. Astrab, A. H. Fauq, J-B. Ousset, S. Trehan, J. Am. Chem. Soc. 1986, 108, 3438-3442;
-
(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 3438-3442
-
-
Tius, M.A.1
Astrab, D.P.2
Fauq, A.H.3
Ousset, J.-B.4
Trehan, S.5
-
26
-
-
0028208455
-
-
e) M. A. Tius, C-K. Kwok, Z-Q. Gu, C. Zhao, Synth. Commun. 1994, 24, 871-885;
-
(1994)
Synth. Commun.
, vol.24
, pp. 871-885
-
-
Tius, M.A.1
Kwok, C.-K.2
Gu, Z.-Q.3
Zhao, C.4
-
28
-
-
0032507922
-
-
g) M. A. Tius, J. Busch-Petersen, M. Yamahita, Tetrahedron Lett. 1998, 39, 4219-4222;
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 4219-4222
-
-
Tius, M.A.1
Busch-Petersen, J.2
Yamahita, M.3
-
29
-
-
0032555424
-
-
h) M. A. Tius, H. Hu, J. K. Kawakami, J. Busch-Petersen, J. Org. Chem. 1998, 63, 5971-5976;
-
(1998)
J. Org. Chem.
, vol.63
, pp. 5971-5976
-
-
Tius, M.A.1
Hu, H.2
Kawakami, J.K.3
Busch-Petersen, J.4
-
32
-
-
4644354709
-
-
note
-
For a straightforward comparison of geometric parameters for the different pentadienyl cations described in the text, the numbering indicated in Scheme 1 for 1 was adopted.
-
-
-
-
33
-
-
0037395377
-
-
See also ref. [9]
-
The oxygen substituents in 1 occupy positions structurally equivalent to those of protonated alkoxyvinylallenal intermediates explored by Tius for rapid construction of the cross-conjugated alkylidene-cyclopentenone cores of several natural products. For a review summarizing Tius' contributions, see: M. A. Tius, Acc. Chem. Res. 2003, 36, 284-290. See also ref. [9].
-
(2003)
Acc. Chem. Res.
, vol.36
, pp. 284-290
-
-
Tius, M.A.1
-
36
-
-
0001641084
-
-
b) I. Morao, B. Lecea, F. P. Cossío, J. Org. Chem. 1997, 62, 7033-7036;
-
(1997)
J. Org. Chem.
, vol.62
, pp. 7033-7036
-
-
Morao, I.1
Lecea, B.2
Cossío, F.P.3
-
37
-
-
0001537387
-
-
c) A. R. de Lera, R. Alvarez, B. Lecea, A. Torrado, F. P. Cossío, Angew. Chem. 2001, 113, 570-574; Angew. Chem. Int. Ed. 2001, 40, 557-561.
-
(2001)
Angew. Chem.
, vol.113
, pp. 570-574
-
-
De Lera, A.R.1
Alvarez, R.2
Lecea, B.3
Torrado, A.4
Cossío, F.P.5
-
38
-
-
0035793296
-
-
c) A. R. de Lera, R. Alvarez, B. Lecea, A. Torrado, F. P. Cossío, Angew. Chem. 2001, 113, 570-574; Angew. Chem. Int. Ed. 2001, 40, 557-561.
-
(2001)
Angew. Chem. Int. Ed.
, vol.40
, pp. 557-561
-
-
-
40
-
-
0000969638
-
-
b) P. von R. Schleyer, T. W. Bentley, W. Koch, A. J. Kos, H. Schwarz, J. Am. Chem. Soc. 1987, 109, 6953-6957.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 6953-6957
-
-
Schleyer, P.V.R.1
Bentley, T.W.2
Koch, W.3
Kos, A.J.4
Schwarz, H.5
-
45
-
-
0000584447
-
-
a) K. N. Houk, Y. Li, J. D. Evanseck, Angew. Chem. 1992, 104, 711-739; Angew. Chem. Int. Ed. 1992, 31, 682-708;
-
(1992)
Angew. Chem.
, vol.104
, pp. 711-739
-
-
Houk, K.N.1
Li, Y.2
Evanseck, J.D.3
-
46
-
-
33748960439
-
-
a) K. N. Houk, Y. Li, J. D. Evanseck, Angew. Chem. 1992, 104, 711-739; Angew. Chem. Int. Ed. 1992, 31, 682-708;
-
(1992)
Angew. Chem. Int. Ed.
, vol.31
, pp. 682-708
-
-
-
47
-
-
0002549529
-
-
b) K. N. Houk, J. González, Y. Li, Acc. Chem. Res. 1995, 28, 81-90.
-
(1995)
Acc. Chem. Res.
, vol.28
, pp. 81-90
-
-
Houk, K.N.1
González, J.2
Li, Y.3
-
48
-
-
0001261240
-
-
The destabilizing cyclic, four-electron interaction is considered to be the most significant stereoelectronic effect determining the outwards torquoselectivity in the electrocyclic ring opening of cyclobutenes substituted with a donor at C3 to afford stereodefined butadienes with E geometries; see: W. R. Jr., Dolbier, H. Koroniak, K. N. Houk, C. Sheu, Acc. Chem. Res. 1996, 29, 471-477.
-
(1996)
Acc. Chem. Res.
, vol.29
, pp. 471-477
-
-
Dolbier Jr., W.R.1
Koroniak, H.2
Houk, K.N.3
Sheu, C.4
-
52
-
-
0000407498
-
-
a) R. Herges, H. Jiao, P. von R. Schleyer, Angew. Chem. 1994, 106, 1441-1444; Angew. Chem. Int. Ed. Engl. 1994, 33, 1376-1378;
-
(1994)
Angew. Chem.
, vol.106
, pp. 1441-1444
-
-
Herges, R.1
Jiao, H.2
Schleyer, P.V.R.3
-
53
-
-
33748238243
-
-
a) R. Herges, H. Jiao, P. von R. Schleyer, Angew. Chem. 1994, 106, 1441-1444; Angew. Chem. Int. Ed. Engl. 1994, 33, 1376-1378;
-
(1994)
Angew. Chem. Int. Ed. Engl.
, vol.33
, pp. 1376-1378
-
-
-
54
-
-
0001104288
-
-
b) H. Jiao, P. v. R. Schleyer, Angew. Chem. 1995, 107, 329-332; Angew. Chem. Int. Ed. Engl. 1995, 34, 334-337;
-
(1995)
Angew. Chem.
, vol.107
, pp. 329-332
-
-
Jiao, H.1
Schleyer, P.V.R.2
-
55
-
-
33748242533
-
-
b) H. Jiao, P. v. R. Schleyer, Angew. Chem. 1995, 107, 329-332; Angew. Chem. Int. Ed. Engl. 1995, 34, 334-337;
-
(1995)
Angew. Chem. Int. Ed. Engl.
, vol.34
, pp. 334-337
-
-
-
57
-
-
4644326241
-
-
note
-
The ring-current model is applied to the transition structure of the Nazarov reaction (3 ts).
-
-
-
-
58
-
-
4644358609
-
-
note
-
A representation of the HOMO of in-7 ts showing the orientation of the oxygen relative to the helical array and its interaction with the forming bond, can be found in the Supporting Information.
-
-
-
-
59
-
-
4644346892
-
-
note
-
These reactions have been described previously at the MP2/6-31G* level of theory (see ref. [15]).
-
-
-
-
61
-
-
4644331456
-
-
note
-
15: qC1 = 0.56457, qC5 = -0.36928; in-15 ts: qC1 = 0.343801, qC5 = -0.48219; out-15: qC1 = 0.55833, qC5 = -0.36905; out-15 ts: qC1 = 0.30818, qC5 = -0.49167.
-
-
-
-
62
-
-
0344443373
-
-
a) W. He, X. Sun, A. Frontier, J. Am. Chem. Soc. 2003, 125, 14278-14279.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 14278-14279
-
-
He, W.1
Sun, X.2
Frontier, A.3
-
63
-
-
0346025411
-
-
2. The donor group at C2 suffices, as shown in: b) G. Liang, S. N. Gradl, D. Trauner, Org. Lett. 2003, 5, 4931-4934.
-
(2003)
Org. Lett.
, vol.5
, pp. 4931-4934
-
-
Liang, G.1
Gradl, S.N.2
Trauner, D.3
-
64
-
-
0004133516
-
-
Gaussian, Inc., Pittsburgh PA
-
Gaussian 98 (Revision A.1.1): M. J. Frisch, G. W. Trucks, H. B. Schlegel, M. A. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D.J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh PA, 2001.
-
(2001)
Gaussian 98 (Revision A.1.1)
-
-
Frisch, M.J.1
Trucks, G.W.2
Schlegel, H.B.3
Scuseria, M.A.4
Robb, M.A.5
Cheeseman, J.R.6
Zakrzewski, V.G.7
Montgomery, J.A.8
Stratmann, R.E.9
Burant, J.C.10
Dapprich, S.11
Millam, J.M.12
Daniels, A.D.13
Kudin, K.N.14
Strain, M.C.15
Farkas, O.16
Tomasi, J.17
Barone, V.18
Cossi, M.19
Cammi, R.20
Mennucci, B.21
Pomelli, C.22
Adamo, C.23
Clifford, S.24
Ochterski, J.25
Petersson, G.A.26
Ayala, P.Y.27
Cui, Q.28
Morokuma, K.29
Salvador, P.30
Dannenberg, J.J.31
Malick, D.K.32
Rabuck, A.D.33
Raghavachari, K.34
Foresman, J.35
Cioslowski, J.36
Ortiz, J.V.37
Baboul, A.G.38
Stefanov, B.B.39
Liu, G.40
Liashenko, A.41
Piskorz, P.42
Komaromi, I.43
Gomperts, R.44
Martin, R.L.45
Fox, D.J.46
Keith, T.47
Al-Laham, M.A.48
Peng, C.Y.49
Nanayakkara, A.50
Challacombe, M.51
Gill, P.M.W.52
Johnson, B.53
Chen, W.54
Wong, M.W.55
Andres, J.L.56
Gonzalez, C.57
Head-Gordon, M.58
Replogle, E.S.59
Pople, J.A.60
more..
-
69
-
-
0345491105
-
-
e) C. Lee, W. Yang, R. G. Parr, 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
-
70
-
-
16444375810
-
-
f) for a description of density functionals as implemented in the Gaussian series of programs, see: B. G. Johnson, P. M. W. Gill, J. A. Pople, J. Chem. Phys. 1993, 98, 5612-5626.
-
(1993)
J. Chem. Phys.
, vol.98
, pp. 5612-5626
-
-
Johnson, B.G.1
Gill, P.M.W.2
Pople, J.A.3
-
71
-
-
0030018945
-
-
E. Goldstein, B. Beno, K. N. Houk, J. Am. Chem. Soc. 1996, 118, 6036-6043.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 6036-6043
-
-
Goldstein, E.1
Beno, B.2
Houk, K.N.3
-
72
-
-
0030816069
-
-
a) T. Suzuki, T. Ohwada, K. Shudo, J. Am. Chem. Soc. 1997, 119, 6774-6780;
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 6774-6780
-
-
Suzuki, T.1
Ohwada, T.2
Shudo, K.3
-
73
-
-
0032550682
-
-
b) T. Ohwada, T. Suzuki, K. Shudo, J. Am. Chem. Soc. 1998, 120, 4629-4637.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 4629-4637
-
-
Ohwada, T.1
Suzuki, T.2
Shudo, K.3
-
77
-
-
0011190497
-
-
P. v. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. v. E. Hommes, J. Am. Chem. Soc. 1996, 118, 6317-6318.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 6317-6318
-
-
Schleyer, P.V.R.1
Maerker, C.2
Dransfeld, A.3
Jiao, H.4
Hommes, N.J.R.V.E.5
-
78
-
-
11744305193
-
-
K. Wolinski, J. F. Hilton, P. Pulay, J. Am. Chem. Soc. 1990, 112, 8251-8260.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 8251-8260
-
-
Wolinski, K.1
Hilton, J.F.2
Pulay, P.3
|