-
3
-
-
0542397750
-
-
Review articles
-
Review articles: (a) Molander, G. Acc. Chem. Res. 1998, 31, 603.
-
(1998)
Acc. Chem. Res.
, vol.31
, pp. 603
-
-
Molander, G.1
-
4
-
-
0026721571
-
-
Eight-Membered carbocycles
-
Eight-Membered carbocycles: (b) Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757.
-
(1992)
Tetrahedron
, vol.48
, pp. 5757
-
-
Petasis, N.A.1
Patane, M.A.2
-
6
-
-
0002174828
-
-
Eight-and nine-membered carbocycles: Atta-ur-Rahman, Ed.; Eisevier: Amsterdam
-
Eight-and nine-membered carbocycles: (d) Oishi, T.; Ohtsuka, Y. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Eisevier: Amsterdam, 1989; Vol. 3, p 73.
-
(1989)
Studies in Natural Products Synthesis
, vol.3
, pp. 73
-
-
Oishi, T.1
Ohtsuka, Y.2
-
7
-
-
0028893499
-
-
Lactones
-
Lactones: (e) Rousseau, G. Tetrahedron 1995, 51, 2777.
-
(1995)
Tetrahedron
, vol.51
, pp. 2777
-
-
Rousseau, G.1
-
8
-
-
0034246704
-
-
Yet, L. Chem. Rev. 2000, 100, 2963.
-
(2000)
Chem. Rev.
, vol.100
, pp. 2963
-
-
Yet, L.1
-
9
-
-
0033618523
-
-
Review articles on radical methods: (a) Yet, L. Tetrahedron 1999, 55, 9349.
-
(1999)
Tetrahedron
, vol.55
, pp. 9349
-
-
Yet, L.1
-
11
-
-
3343012187
-
-
Reviews on the development and various applications of the alkene metathesis reaction: (a) Grubbs, R. H. Tetrahedron 2004, 60, 7117.
-
(2004)
Tetrahedron
, vol.60
, pp. 7117
-
-
Grubbs, R.H.1
-
12
-
-
0142023994
-
-
(b) Schrock, R. R., Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 4592
-
-
Schrock, R.R.1
Hoveyda, A.H.2
-
15
-
-
0038215596
-
-
(e) Blechert, S.; Connon, S. J. Angew. Chem., Int. Ed. 2003, 42, 1900.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 1900
-
-
Blechert, S.1
Connon, S.J.2
-
16
-
-
0032580376
-
-
For review articles on RCM, see
-
For review articles on RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
-
(1998)
Tetrahedron
, vol.54
, pp. 4413
-
-
Grubbs, R.H.1
Chang, S.2
-
19
-
-
0034674322
-
-
For a short review on the application of RCM in the synthesis of medium-sized rings, see: (a) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 2073
-
-
Maier, M.E.1
-
20
-
-
33749026617
-
-
Review on the application of RCM macrocyclizations in the total synthesis of natural products: (b) Gradillas, A.; Perez-Castells, J. Angew. Chem., Int. Ed. 2006, 45, 6086.
-
(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 6086
-
-
Gradillas, A.1
Perez-Castells, J.2
-
21
-
-
0842306918
-
-
However, attempts to generalize these observations have not met success; see, for example: Vassilikogiannakis, G.; Margaros, I.; Tofi, M. Org. Lett. 2004, 6, 205.
-
(2004)
Org. Lett.
, vol.6
, pp. 205
-
-
Vassilikogiannakis, G.1
Margaros, I.2
Tofi, M.3
-
22
-
-
0037009040
-
-
Compare the conclusions from this reference to the following: Nicolaou, K. C; Vassilikogiannakis, G.; Montagnon, T. Angew. Chem., Int. Ed. 2002, 41, 3276.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 3276
-
-
Nicolaou, K.C.1
Vassilikogiannakis, G.2
Montagnon, T.3
-
23
-
-
0000037017
-
-
Bourgeois, D.; Pancrazi, A.; Ricard, L.; Prunet, J. Angew. Chem., Int. Ed. 2000, 39, 726.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 726
-
-
Bourgeois, D.1
Pancrazi, A.2
Ricard, L.3
Prunet, J.4
-
25
-
-
13244291529
-
-
Cycloalkene
-
Cycloalkene: (b) Castoldi, D.; Caggiano, L.; Panigada, L.; Sharon, O.; Costa, A. M.; Gennari, C. Angew. Chem., Int. Ed. 2005, 44, 588.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 588
-
-
Castoldi, D.1
Caggiano, L.2
Panigada, L.3
Sharon, O.4
Costa, A.M.5
Gennari, C.6
-
26
-
-
0032513726
-
-
Lactam
-
Lactam: (c) Fink, B. E.; Kym, P. R.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1998, 120, 4334.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 4334
-
-
Fink, B.E.1
Kym, P.R.2
Katzenellenbogen, J.A.3
-
27
-
-
0037134804
-
-
Laetone
-
Laetone: (d) Furstner, A.; Radkowski, K.; Wirtz, C; Goddard, R.; Lehmann, C.; Mynott, R. J. Am. Chem. Soc. 2002, 124, 7061.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 7061
-
-
Furstner, A.1
Radkowski, K.2
Wirtz, C.3
Goddard, R.4
Lehmann, C.5
Mynott, R.6
-
28
-
-
0032482544
-
-
11-Membered rings
-
11-Membered rings: (e) El Sukkari, H.; Gesson, J. P.; Renoux, B. Tetrahedron Lett. 1998, 39, 4043.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 4043
-
-
El Sukkari, H.1
Gesson, J.P.2
Renoux, B.3
-
29
-
-
0033516688
-
-
(f) Winkler, J. D.; Holland, J. M.; Kasparec, J.; Axelsen, P. H. Tetrahedron 1999, 55, 8199.
-
(1999)
Tetrahedron
, vol.55
, pp. 8199
-
-
Winkler, J.D.1
Holland, J.M.2
Kasparec, J.3
Axelsen, P.H.4
-
30
-
-
0034697702
-
-
(g) Arisawa, M.; Kato, C.; Kaneko, H.; Nishida, A.; Nakagawa, M. J. Chem. Soc., Perkin Trans 1, 2000, 1873.
-
(2000)
J. Chem. Soc., Perkin Trans 1
, pp. 1873
-
-
Arisawa, M.1
Kato, C.2
Kaneko, H.3
Nishida, A.4
Nakagawa, M.5
-
32
-
-
0035859315
-
-
12-Membered rings
-
12-Membered rings: (i) Snider, B. B.; Song, F. Org. Lett. 2001, 3, 1817.
-
(2001)
Org. Lett.
, vol.3
, pp. 1817
-
-
Snider, B.B.1
Song, F.2
-
33
-
-
0037012401
-
-
(j) Wu, Y.; Liao, X.; Wang, R.; Xie, X.-S.; De Brabander, J. K. J. Am. Chem. Soc. 2002, 124, 3245.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 3245
-
-
Wu, Y.1
Liao, X.2
Wang, R.3
Xie, X.-S.4
De Brabander, J.K.5
-
34
-
-
1642569116
-
-
(k) Couladouros, E. A.; Mihou, A. P.; Bouzas, E. A. Org. Lett. 2004, 6, 977.
-
(2004)
Org. Lett.
, vol.6
, pp. 977
-
-
Couladouros, E.A.1
Mihou, A.P.2
Bouzas, E.A.3
-
35
-
-
0034680663
-
-
14-Membered rings
-
14-Membered rings: (l) Furstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 7990
-
-
Furstner, A.1
Thiel, O.R.2
Kindler, N.3
Bartkowska, B.4
-
36
-
-
0032500161
-
-
(m) Goldring, W. P. D.; Hodder, A. S.; Weiler, L. Tetrahedron Lett. 1998, 39, 4955.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 4955
-
-
Goldring, W.P.D.1
Hodder, A.S.2
Weiler, L.3
-
37
-
-
0037134804
-
-
(a) Furstner, A.; Radkowski, K.; Wirtz, C.; Goddard, R.; Lehman, C. W.; Minott, R. J. Am. Chem. Soc. 2002, 124, 7061.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 7061
-
-
Furstner, A.1
Radkowski, K.2
Wirtz, C.3
Goddard, R.4
Lehman, C.W.5
Minott, R.6
-
40
-
-
0030755282
-
-
Numerous examples in the 16-membered series come from synthetic studies toward epothilones, where undesired (E)-products usually predominate: (a) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Roschangar, F.; Saurabia, F.; Ninkovic, S.; Yang, Z.; Trujillo, J. I. J. Am. Chem. Soc. 1997, 119, 7960.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 7960
-
-
Nicolaou, K.C.1
He, Y.2
Vourloumis, D.3
Vallberg, H.4
Roschangar, F.5
Saurabia, F.6
Ninkovic, S.7
Yang, Z.8
Trujillo, J.I.9
-
41
-
-
1442285541
-
-
(b) Rivkin, A.; Cho, Y. S.; Gabarda, A. E.; Yoshimura, F.; Danishefsky, S. J. J. Nat. Prod. 2004, 67, 139.
-
(2004)
J. Nat. Prod.
, vol.67
, pp. 139
-
-
Rivkin, A.1
Cho, Y.S.2
Gabarda, A.E.3
Yoshimura, F.4
Danishefsky, S.J.5
-
42
-
-
0030894922
-
-
(c) Schinzer, D.; Limberg, A.; Bauer, A.; Bohm, O. M.; Cordes, M. Angew. Chem., Int. Ed. 1997, 36, 523.
-
(1997)
Angew. Chem., Int. Ed.
, vol.36
, pp. 523
-
-
Schinzer, D.1
Limberg, A.2
Bauer, A.3
Bohm, O.M.4
Cordes, M.5
-
44
-
-
0034141369
-
-
Nakashima, K.; Ito, R.; Sono, M.; Tori, M. Heterocycles 2000, 53, 301.
-
(2000)
Heterocycles
, vol.53
, pp. 301
-
-
Nakashima, K.1
Ito, R.2
Sono, M.3
Tori, M.4
-
45
-
-
0038373087
-
-
Corrigendum: Prunet, J. Angew. Chem., Int. Ed. 2003, 42, 3322
-
Prunet, J. Angew. Chem., Int. Ed. 2003, 42, 2826. Corrigendum: Prunet, J. Angew. Chem., Int. Ed. 2003, 42, 3322.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 2826
-
-
Prunet, J.1
-
46
-
-
20444381357
-
-
(a) Furstner, A.; Turet, L. Angew. Chem., Int. Ed. 2005, 44, 3462.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 3462
-
-
Furstner, A.1
Turet, L.2
-
48
-
-
0038584256
-
-
(c) Furstner, A.; Grela, K. Angew. Chem., Int. Ed. 2000, 39, 1234.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 1234
-
-
Furstner, A.1
Grela, K.2
-
51
-
-
0037007930
-
-
(b) Rodriguez, J. R.; Castedo, L.; Mascarenas, J. L. Chem. - Eur. J. 2002, 8, 2923.
-
(2002)
Chem. - Eur. J.
, vol.8
, pp. 2923
-
-
Rodriguez, J.R.1
Castedo, L.2
Mascarenas, J.L.3
-
52
-
-
0035812732
-
-
See also
-
See also: (c) Balskus, E. P.; Mendez-Andino, J.; Arbit, R. M.; Paquette, L. A. J. Org. Chem. 2001, 66, 6695.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 6695
-
-
Balskus, E.P.1
Mendez-Andino, J.2
Arbit, R.M.3
Paquette, L.A.4
-
54
-
-
2542459241
-
-
Ivkovic, A.; Matovic, R.; Saicic, R. N. Org. Lett. 2004, 6, 1221.
-
(2004)
Org. Lett.
, vol.6
, pp. 1221
-
-
Ivkovic, A.1
Matovic, R.2
Saicic, R.N.3
-
55
-
-
0034743053
-
-
(a) Aburel, P. S.; Romming, C.; Ma. K.; Undheim, K. J. Chem. Soc., Perkin Trans. 1 2001, 1458.
-
(2001)
J. Chem. Soc., Perkin Trans. 1
, pp. 1458
-
-
Aburel, P.S.1
Romming, C.2
Ma, K.3
Undheim, K.4
-
56
-
-
1542375287
-
-
(b) Fraga, C. A. M.; Teixeira, L. H. P.; Menezes, C. M.; Sant'Anna, C. M. R.; Conceicao, M.; Ramos, K. V.; de Aquino Neto, F.; Barreiro, E. J. Tetrahedron 2004, 60, 2745.
-
(2004)
Tetrahedron
, vol.60
, pp. 2745
-
-
Fraga, C.A.M.1
Teixeira, L.H.P.2
Menezes, C.M.3
Sant'Anna, C.M.R.4
Conceicao, M.5
Ramos, K.V.6
De Aquino Neto, F.7
Barreiro, E.J.8
-
58
-
-
0001855961
-
-
Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 110.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 110
-
-
Schwab, P.1
Grubbs, R.H.2
Ziller, J.W.3
-
59
-
-
0033598258
-
-
Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
-
(1999)
Org. Lett.
, vol.1
, pp. 953
-
-
Scholl, M.1
Ding, S.2
Lee, C.W.3
Grubbs, R.H.4
-
60
-
-
33845529555
-
-
note
-
Other bases, such as DBU. NaH, or metal alkoxides, were not successful.
-
-
-
-
61
-
-
0000873998
-
-
Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K.
-
However, examples are known where the fragmentation is successful even when this stereoelectronic requirement is not fulfilled; for a review article on Grob fragmentation, see: Weyerstahl, P.; Marschall, H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991: Vol. 6, p 1041.
-
(1991)
Comprehensive Organic Synthesis
, vol.6
, pp. 1041
-
-
Weyerstahl, P.1
Marschall, H.2
-
62
-
-
33845535353
-
-
note
-
Other bases, such as potassium ethoxide, potassium tert-butoxide, sodium hydride, DBU, potassium carbonate/18-crown-6. or potassium hydroxide/18-crown-6, were unsuccessful.
-
-
-
-
63
-
-
33845530045
-
-
note
-
In the case of compounds 3a-c, the bicyclic system is thermodynamically favored and the fragmentation step cannot be performed as a simple retro-aldol reaction.
-
-
-
-
64
-
-
0001688315
-
-
Hirama, M.; Noda, T.; Takeishi, S.; Ito, S. Bull. Chem. Soc. Jpn. 1988, 61, 2645.
-
(1988)
Bull. Chem. Soc. Jpn.
, vol.61
, pp. 2645
-
-
Hirama, M.1
Noda, T.2
Takeishi, S.3
Ito, S.4
-
65
-
-
33947482234
-
-
See the Supporting Information for details
-
The stereochemistry of compounds 11 and 12 was established in the following way: on oxidation with PDC both 12 syn and 12 anti were converted into the same ketone (15): this compound was then subjected to hydrogenation of the alkene bond over Pd/C to give the trans-decalone derivative described in the literature: Wharton, P. S.; Hiegel, G. A. J. Org. Chem. 1965, 30, 3254. See the Supporting Information for details.
-
(1965)
J. Org. Chem.
, vol.30
, pp. 3254
-
-
Wharton, P.S.1
Hiegel, G.A.2
-
66
-
-
33845539393
-
-
note
-
These results were obtained with the stereochemically defined isomers 12 syn and 12 anti, purified by column chromatography and separately characterized. The whole sequence of reactions was also performed with the diastereomeric mixture, without the separation of the isomers, with similar results.
-
-
-
-
69
-
-
0041750605
-
-
Atta-ur-Rahman, Ed.; Elsevier: Amsterdam
-
Czyzewska, E.; Oehlschlager, A. C. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1991; Vol. 8, p. 219.
-
(1991)
Studies in Natural Products Chemistry
, vol.8
, pp. 219
-
-
Czyzewska, E.1
Oehlschlager, A.C.2
-
70
-
-
0025214349
-
-
and the references therein
-
(a) Persoons, C. J.; Ritter, F. J.; Verwiel, P. E.; Hauptmenn, H.; Mori, K. Tetrahedron Lett. 1990, 31, 1747, and the references therein.
-
(1990)
Tetrahedron Lett.
, vol.31
, pp. 1747
-
-
Persoons, C.J.1
Ritter, F.J.2
Verwiel, P.E.3
Hauptmenn, H.4
Mori, K.5
-
72
-
-
0023890324
-
-
Total syntheses of Periplanone C: (a) Shizuri, Y.; Matsunaga, K.; Tamaki, K.; Yamaguchi, S.; Yamamura, S. Tetrahedron Lett. 1988, 29, 1971.
-
(1988)
Tetrahedron Lett.
, vol.29
, pp. 1971
-
-
Shizuri, Y.1
Matsunaga, K.2
Tamaki, K.3
Yamaguchi, S.4
Yamamura, S.5
-
74
-
-
0030915732
-
-
(c) Nishii, Y.; Watanabe, K.; Yoshida, T.; Okayama, T.; Takahashi, S.; Tanabe, Y. Tetrahedron 1997, 53, 7209.
-
(1997)
Tetrahedron
, vol.53
, pp. 7209
-
-
Nishii, Y.1
Watanabe, K.2
Yoshida, T.3
Okayama, T.4
Takahashi, S.5
Tanabe, Y.6
-
75
-
-
33845523942
-
-
U.S. Patent 4,939,275
-
Hofmeister, P.; Krieg, W.; Neudert, R.; Hauptmann, H. U.S. Patent 4,939,275.
-
-
-
Hofmeister, P.1
Krieg, W.2
Neudert, R.3
Hauptmann, H.4
-
76
-
-
0346847440
-
-
Biendl, M.; Hauptmann, H.; Sass, H. Tetrahedron Lett. 1989, 30, 2367.
-
(1989)
Tetrahedron Lett.
, vol.30
, pp. 2367
-
-
Biendl, M.1
Hauptmann, H.2
Sass, H.3
-
77
-
-
2542486030
-
-
Shirley, D. A.; Harmon, T. E.; Cheng, C. F. J. Organometal. Chem. 1974, 69, 323.
-
(1974)
J. Organometal. Chem.
, vol.69
, pp. 323
-
-
Shirley, D.A.1
Harmon, T.E.2
Cheng, C.F.3
-
78
-
-
0000204956
-
-
Hook, J. M.; Mander, L. N.; Woolias, M. Tetrahedron Lett. 1982, 23, 1095.
-
(1982)
Tetrahedron Lett.
, vol.23
, pp. 1095
-
-
Hook, J.M.1
Mander, L.N.2
Woolias, M.3
-
79
-
-
33845543169
-
-
note
-
In this case, the fragmentation step could be performed under radical conditions, which would require some additional steps though.
-
-
-
-
80
-
-
0042706825
-
-
A review article on the alkene (E)-(Z) isomerization: Dugave, C.; Demange, L. Chem. Rev. 2003, 103, 2475.
-
(2003)
Chem. Rev.
, vol.103
, pp. 2475
-
-
Dugave, C.1
Demange, L.2
-
81
-
-
0034814705
-
-
Ferreri, C.; Costantino, C.; Perrotta, L.; Landi, L.; Mulazzani, Q. G.; Chatgilialoglu, C. J. Am. Chem. Soc. 2001, 123, 4459.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 4459
-
-
Ferreri, C.1
Costantino, C.2
Perrotta, L.3
Landi, L.4
Mulazzani, Q.G.5
Chatgilialoglu, C.6
-
82
-
-
0033484573
-
-
Triene 28 possesses four allylic hydrogen atoms sterically available for the abstraction, both electron-deficient (a to the carbonyl group) and electron-rich (a to the two-methylene group). For a review article on polarity reversal catalysis in hydrogen abstraction reactions, see: Roberts, B. P. Chem. Soc. Rev. 1999, 28, 25.
-
(1999)
Chem. Soc. Rev.
, vol.28
, pp. 25
-
-
Roberts, B.P.1
-
87
-
-
33845518217
-
-
note
-
13C NMR spectrum identical to the spectrum previously reported in ref 34c.
-
-
-
-
88
-
-
0000204956
-
-
Hook, J. M.; Mander, L. N.; Woolias, M. Tetrahedron Lett. 1982, 23, 1095.
-
(1982)
Tetrahedron Lett.
, vol.23
, pp. 1095
-
-
Hook, J.M.1
Mander, L.N.2
Woolias, M.3
|