-
1
-
-
8744279305
-
-
For selected reviews on the synthesis of macrocycles, see: a
-
For selected reviews on the synthesis of macrocycles, see: (a) Wessjohann, L. A.; Ruijter, E. Top. Curr. Chem. 2005, 243, 137.
-
(2005)
Top. Curr. Chem
, vol.243
, pp. 137
-
-
Wessjohann, L.A.1
Ruijter, E.2
-
2
-
-
0034246704
-
-
(b) Yet, L. Chem. Rev. 2000, 100, 2963.
-
(2000)
Chem. Rev
, vol.100
, pp. 2963
-
-
Yet, L.1
-
5
-
-
34250686411
-
-
107. For a discussion of the role of strain in macrocyclic ring closure, see
-
(e) Meng, Q.; Hesse, M. Top. Curr. Chem. 1992, 161, 107. For a discussion of the role of strain in macrocyclic ring closure, see:
-
(1992)
Top. Curr. Chem
, vol.161
-
-
Meng, Q.1
Hesse, M.2
-
7
-
-
0000851696
-
-
Trost, B. M, Fleming, I, Heathcock, C. H, Eds, Pergamon Press: Oxford
-
Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 133.
-
(1991)
Comprehensive Organic Synthesis
, vol.2
, pp. 133
-
-
Heathcock, C.H.1
-
8
-
-
0001006137
-
-
For selected references relating to macroaldolization processes, see: a
-
For selected references relating to macroaldolization processes, see: (a) Tsuji, J.; Yamada, T.; Kaito, M.; Mandai, T. Bull. Chem. Soc. Jpn. 1980, 53, 1417.
-
(1980)
Bull. Chem. Soc. Jpn
, vol.53
, pp. 1417
-
-
Tsuji, J.1
Yamada, T.2
Kaito, M.3
Mandai, T.4
-
9
-
-
0019178984
-
-
(b) Robin, J. P.; Gringore, O.; Brown, E. Tetrahedron Lett. 1980, 21, 2709.
-
(1980)
Tetrahedron Lett
, vol.21
, pp. 2709
-
-
Robin, J.P.1
Gringore, O.2
Brown, E.3
-
10
-
-
84987293949
-
-
(c) Vögtle, F.; Mayenfels, P.; Luppertz, F. Synthesis 1984, 7, 580.
-
(1984)
Synthesis
, vol.7
, pp. 580
-
-
Vögtle, F.1
Mayenfels, P.2
Luppertz, F.3
-
11
-
-
34250660755
-
-
(d) Kuroda, S.; Maeda, S.; Hirooka, S.; Ogisu, M.; Yamazaki, K.; Shimao, I.; Yasunami, M. Tetrahedron Lett. 1989, 30, 1557.
-
(1989)
Tetrahedron Lett
, vol.30
, pp. 1557
-
-
Kuroda, S.1
Maeda, S.2
Hirooka, S.3
Ogisu, M.4
Yamazaki, K.5
Shimao, I.6
Yasunami, M.7
-
12
-
-
0027495167
-
-
(e) Hayward, C. M.; Yohannes, D.; Danishefsky, S. J. J. Am. Chem. Soc. 1993, 115, 9345.
-
(1993)
J. Am. Chem. Soc
, vol.115
, pp. 9345
-
-
Hayward, C.M.1
Yohannes, D.2
Danishefsky, S.J.3
-
13
-
-
0028287921
-
-
(f) Romero, M. A.; Franco, R. P.; Cruz-Almanza, R.; Padilla, F. Tetrahedron Lett. 1994, 35, 3255.
-
(1994)
Tetrahedron Lett
, vol.35
, pp. 3255
-
-
Romero, M.A.1
Franco, R.P.2
Cruz-Almanza, R.3
Padilla, F.4
-
14
-
-
0029609027
-
-
(g) Takao, K.; Ochiai, H.; Yoshida, K.; Hashizuka, T.; Koshimura, H.; Tadano, K.; Ogawa, S. J. Org. Chem. 1995, 60, 8179.
-
(1995)
J. Org. Chem
, vol.60
, pp. 8179
-
-
Takao, K.1
Ochiai, H.2
Yoshida, K.3
Hashizuka, T.4
Koshimura, H.5
Tadano, K.6
Ogawa, S.7
-
15
-
-
0029611717
-
-
(h) Toshima, K.; Ohta, K.; Yanagawa, K.; Kano, T.; Nakata, M.; Kinoshita, M.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 10825.
-
(1995)
J. Am. Chem. Soc
, vol.117
, pp. 10825
-
-
Toshima, K.1
Ohta, K.2
Yanagawa, K.3
Kano, T.4
Nakata, M.5
Kinoshita, M.6
Matsumura, S.7
-
16
-
-
0029929386
-
-
(i) Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Tetrahedron 1996, 52, 6283.
-
(1996)
Tetrahedron
, vol.52
, pp. 6283
-
-
Magnus, P.1
Carter, R.2
Davies, M.3
Elliott, J.4
Pitterna, T.5
-
17
-
-
0030669587
-
-
(j) Meng, D.; Bertinato, P.; Balog, A.; Su, D.-S.; Kamenecka, T.; Sorensen, E. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10073.
-
(1997)
J. Am. Chem. Soc
, vol.119
, pp. 10073
-
-
Meng, D.1
Bertinato, P.2
Balog, A.3
Su, D.-S.4
Kamenecka, T.5
Sorensen, E.J.6
Danishefsky, S.J.7
-
18
-
-
0030786385
-
-
(k) Katoh, T.; Nagata, Y.; Yoshino, T.; Nakatani, S.; Terashima, S. Tetrahedron 1997, 53, 10253.
-
(1997)
Tetrahedron
, vol.53
, pp. 10253
-
-
Katoh, T.1
Nagata, Y.2
Yoshino, T.3
Nakatani, S.4
Terashima, S.5
-
19
-
-
0033605315
-
-
(l) Caddick, S.; Delisser, V. M.; Doyle, V. E.; Khan, S.; Avent, A. G.; Vile, S. Tetrahedron 1999, 55, 2737.
-
(1999)
Tetrahedron
, vol.55
, pp. 2737
-
-
Caddick, S.1
Delisser, V.M.2
Doyle, V.E.3
Khan, S.4
Avent, A.G.5
Vile, S.6
-
20
-
-
0002857938
-
-
(m) Wei, C.-Q.; Zhao, G.; Jiang, X.-R.; Ding, Y. Chem. Soc., Perkin Trans. 1 1999, 3531.
-
(1999)
Chem. Soc., Perkin Trans. 1
, pp. 3531
-
-
Wei, C.-Q.1
Zhao, G.2
Jiang, X.-R.3
Ding, Y.4
-
21
-
-
0037700759
-
-
(n) Rassu, G.; Auzzas, L.; Pinna, L.; Zambrano, V.; Zanardi, F.; Battistini, L.; Gaetani, E.; Curti, C.; Casiraghi, G. J. Org. Chem. 2003, 68, 5881.
-
(2003)
J. Org. Chem
, vol.68
, pp. 5881
-
-
Rassu, G.1
Auzzas, L.2
Pinna, L.3
Zambrano, V.4
Zanardi, F.5
Battistini, L.6
Gaetani, E.7
Curti, C.8
Casiraghi, G.9
-
22
-
-
0000523045
-
-
For Mukaiyama and Reformatsky macrocyclizations, see: a
-
For Mukaiyama and Reformatsky macrocyclizations, see: (a) Maruoka, K.; Hashimoto, S.; Kitagawa, Y.; Yamamoto, H.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 7705.
-
(1977)
J. Am. Chem. Soc
, vol.99
, pp. 7705
-
-
Maruoka, K.1
Hashimoto, S.2
Kitagawa, Y.3
Yamamoto, H.4
Nozaki, H.5
-
23
-
-
0001485762
-
-
(b) Smith, A. B.; Gauciaro, M. A.; Schow, S. R.; Wovkulich, P. M.; Toder, B. H.; Hall, T. W. J. Am. Chem. Soc. 1981, 103, 219.
-
(1981)
J. Am. Chem. Soc
, vol.103
, pp. 219
-
-
Smith, A.B.1
Gauciaro, M.A.2
Schow, S.R.3
Wovkulich, P.M.4
Toder, B.H.5
Hall, T.W.6
-
24
-
-
0001184830
-
-
(c) Tabuchi, T.; Kawamura, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 33, 3889.
-
(1986)
Tetrahedron Lett
, vol.33
, pp. 3889
-
-
Tabuchi, T.1
Kawamura, K.2
Inanaga, J.3
Yamaguchi, M.4
-
26
-
-
0032959568
-
-
(e) Mukaiyama, T.; Shiina, I.; Iwadare, H.; Saitoh, M.; Nishimura, T.; Ohkawa, N. Sakoh, H.; Nishimura, K.; Tani, Y.; Hasegawa, M.; Yamada, K.; Saitoh, K. Chem.-Eur. J. 1999, 5, 121.
-
(1999)
Chem.-Eur. J
, vol.5
, pp. 121
-
-
Mukaiyama, T.1
Shiina, I.2
Iwadare, H.3
Saitoh, M.4
Nishimura, T.5
Ohkawa, N.6
Sakoh, H.7
Nishimura, K.8
Tani, Y.9
Hasegawa, M.10
Yamada, K.11
Saitoh, K.12
-
27
-
-
0033601166
-
-
(f) Inoue, M.; Sasaki, M.; Tachibana, K. J. Org. Chem. 1999, 64, 9416.
-
(1999)
J. Org. Chem
, vol.64
, pp. 9416
-
-
Inoue, M.1
Sasaki, M.2
Tachibana, K.3
-
28
-
-
0034337671
-
-
(g) Hachiya, I.; Kobayashi, N.; Kijima, H.; Pudhom, K.; Mukaiyama, T. Chem. Lett. 2000, 8, 932.
-
(2000)
Chem. Lett
, vol.8
, pp. 932
-
-
Hachiya, I.1
Kobayashi, N.2
Kijima, H.3
Pudhom, K.4
Mukaiyama, T.5
-
30
-
-
0141739284
-
-
(i) Kigoshi, H.; Kita, M.; Ogawa, S.; Itoh, M.; Uemura, D. Org. Lett. 2003, 5, 957.
-
(2003)
Org. Lett
, vol.5
, pp. 957
-
-
Kigoshi, H.1
Kita, M.2
Ogawa, S.3
Itoh, M.4
Uemura, D.5
-
31
-
-
2942536806
-
-
(j) Nagamitsu, T.; Takano, D.; Fukuda, T.; Otoguro, K.; Kuwajima, I.; Harigaya, Y.; Omura, S. Org. Lett. 2004, 6, 1865.
-
(2004)
Org. Lett
, vol.6
, pp. 1865
-
-
Nagamitsu, T.1
Takano, D.2
Fukuda, T.3
Otoguro, K.4
Kuwajima, I.5
Harigaya, Y.6
Omura, S.7
-
32
-
-
0033690703
-
-
For reviews on the vinylogous aldol reaction, see: a
-
For reviews on the vinylogous aldol reaction, see: (a) Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 100, 1929.
-
(2000)
Chem. Rev
, vol.100
, pp. 1929
-
-
Casiraghi, G.1
Zanardi, F.2
Appendino, G.3
Rassu, G.4
-
33
-
-
23044486219
-
-
(b) Denmark, S. E.; Heemstra, J. R.; Beutner, G. L. Angew. Chem., Int. Ed. 2005, 44, 4682.
-
(2005)
Angew. Chem., Int. Ed
, vol.44
, pp. 4682
-
-
Denmark, S.E.1
Heemstra, J.R.2
Beutner, G.L.3
-
34
-
-
0032481355
-
-
(a) Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813.
-
(1998)
J. Am. Chem. Soc
, vol.120
, pp. 813
-
-
Saito, S.1
Shiozawa, M.2
Ito, M.3
Yamamoto, H.4
-
35
-
-
0033553845
-
-
(b) Saito, S.; Shiozawa, M.; Yamamoto, H. Angew. Chem., Int. Ed. 1999, 38, 1769.
-
(1999)
Angew. Chem., Int. Ed
, vol.38
, pp. 1769
-
-
Saito, S.1
Shiozawa, M.2
Yamamoto, H.3
-
36
-
-
0034674920
-
-
(c) Saito, S.; Shiozawa, M.; Nagahara, T.; Nakadai, M.; Yamamoto, H. J. Am. Chem. Soc. 2000, 122, 7847.
-
(2000)
J. Am. Chem. Soc
, vol.122
, pp. 7847
-
-
Saito, S.1
Shiozawa, M.2
Nagahara, T.3
Nakadai, M.4
Yamamoto, H.5
-
37
-
-
0038288697
-
-
(d) Saito, S.; Nagahara, T.; Shiozawa, M.; Nakadai, M.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6200.
-
(2003)
J. Am. Chem. Soc
, vol.125
, pp. 6200
-
-
Saito, S.1
Nagahara, T.2
Shiozawa, M.3
Nakadai, M.4
Yamamoto, H.5
-
38
-
-
1642389115
-
-
For an asymmetric variation, see
-
(e) For an asymmetric variation, see: Takikawa, H.; Ishihara, K.; Saito, S.; Yamamoto, H. Synlett 2004, 732.
-
(2004)
Synlett
, pp. 732
-
-
Takikawa, H.1
Ishihara, K.2
Saito, S.3
Yamamoto, H.4
-
39
-
-
0029609027
-
-
For an example of an intramolecular vinylogous aldol reaction, see
-
For an example of an intramolecular vinylogous aldol reaction, see: Takao, K.-i.; Hiroshi, O.; Yoshida, K.-i.; Hashizuka, T.; Koshimura, H.; Tadano, K.-i.; Ogawa, S. J. Org. Chem. 1995, 60, 8179.
-
(1995)
J. Org. Chem
, vol.60
, pp. 8179
-
-
Takao, K.-I.1
Hiroshi, O.2
Yoshida, K.-I.3
Hashizuka, T.4
Koshimura, H.5
Tadano, K.-I.6
Ogawa, S.7
-
40
-
-
34250622231
-
-
See the Supporting Information for details
-
See the Supporting Information for details.
-
-
-
-
41
-
-
34250615703
-
-
3Al (1 equiv) with 2,6diphenylphenol (3 equiv). See Supporting Information or ref 6a for details.
-
3Al (1 equiv) with 2,6diphenylphenol (3 equiv). See Supporting Information or ref 6a for details.
-
-
-
-
42
-
-
34250679947
-
-
Varying amounts of starting material and unidentified side products were observed in these reactions
-
Varying amounts of starting material and unidentified side products were observed in these reactions.
-
-
-
-
43
-
-
34250670188
-
-
For details, see the general cyclization procedure in the Supporting Information
-
For details, see the general cyclization procedure in the Supporting Information.
-
-
-
-
44
-
-
34250617278
-
-
Crystallographic data for the 3,5-dinitrobenzoates 14 and 15 can be found in the Supporting Information. The stereochemistry of compound 5 was assigned by analogy.
-
Crystallographic data for the 3,5-dinitrobenzoates 14 and 15 can be found in the Supporting Information. The stereochemistry of compound 5 was assigned by analogy.
-
-
-
-
45
-
-
34250633805
-
-
Crystallographic data for the 3,5-dinitrobenzoate 16 can be found in the Supporting Information. The stereochemistry of compound 8 was assigned by analogy.
-
Crystallographic data for the 3,5-dinitrobenzoate 16 can be found in the Supporting Information. The stereochemistry of compound 8 was assigned by analogy.
-
-
-
-
46
-
-
34250636921
-
-
The stereochemistry of compound 11 was assigned by analogy.
-
The stereochemistry of compound 11 was assigned by analogy.
-
-
-
-
48
-
-
0012045936
-
-
Chandrasekharan, J.; Ramachandran, P. V.; Brown, H. C. J. Org. Chem. 1985, 50, 5446.
-
(1985)
J. Org. Chem
, vol.50
, pp. 5446
-
-
Chandrasekharan, J.1
Ramachandran, P.V.2
Brown, H.C.3
|