-
1
-
-
0004220870
-
-
For numerous examples, see:, 1st ed.; Wiley-VCH, New York
-
For numerous examples, see: Nicolaou, K. C. and Sorensen, E. J. Classics in Total Synthesis, 1st ed.; Wiley-VCH, New York, 1996.
-
(1996)
Classics in Total Synthesis
-
-
Nicolaou, K.C.1
Sorensen, E.J.2
-
5
-
-
34547166889
-
-
Steven, A. and Overman, L. E. Angew. Chem., Int. Ed. 2007, 46, 5488
-
(2007)
Angew. Chem., Int. Ed.
, vol.46
, pp. 5488
-
-
Steven, A.1
Overman, L.E.2
-
6
-
-
54249145967
-
-
Mulzer, J., Gaich, T., and Siengalewicz, P. Angew. Chem., Int. Ed. 2008, 47, 8170
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 8170
-
-
Mulzer, J.1
Gaich, T.2
Siengalewicz, P.3
-
7
-
-
33749387172
-
-
Ed.; Academic Press: San Diego
-
Kam, T. S. and Choo, Y. M. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 2006; Vol. 63, pp 181 - 337.
-
(2006)
The Alkaloids
, vol.63
, pp. 181-337
-
-
Kam, T.S.1
Choo, Y.M.2
Cordell, G.A.3
-
8
-
-
67949110944
-
-
Vinblastine
-
Vinblastine: Ishikawa, H., Colby, D. A., Seto, S., Va, P., Tam, A., Kakei, H., Rayl, T. J., Hwang, I., and Boger, D. L. J. Am. Chem. Soc. 2009, 131, 4904
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 4904
-
-
Ishikawa, H.1
Colby, D.A.2
Seto, S.3
Va, P.4
Tam, A.5
Kakei, H.6
Rayl, T.J.7
Hwang, I.8
Boger, D.L.9
-
9
-
-
0037070544
-
-
Yokoshima, S., Ueda, T., Kobayashi, S., Sato, A., Kuboyama, T., Tokuyama, H., and Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 2137
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 2137
-
-
Yokoshima, S.1
Ueda, T.2
Kobayashi, S.3
Sato, A.4
Kuboyama, T.5
Tokuyama, H.6
Fukuyama, T.7
-
10
-
-
0018388614
-
-
Mangeney, P., Andriamialisoa, R. Z., Langlois, N., Langlois, Y., and Potier, P. J. Am. Chem. Soc. 1979, 101, 2243
-
(1979)
J. Am. Chem. Soc.
, vol.101
, pp. 2243
-
-
Mangeney, P.1
Andriamialisoa, R.Z.2
Langlois, N.3
Langlois, Y.4
Potier, P.5
-
11
-
-
0000352444
-
-
Kutney, J. P., Choi, L. S. L., Nakano, J., Tsukamoto, H., McHugh, M., and Boulet, C. A. Heterocycles 1988, 27, 1845
-
(1988)
Heterocycles
, vol.27
, pp. 1845
-
-
Kutney, J.P.1
Choi, L.S.L.2
Nakano, J.3
Tsukamoto, H.4
McHugh, M.5
Boulet, C.A.6
-
12
-
-
0025980121
-
-
Kuehne, M. E., Matson, P. A., and Bornmann, W. G. J. Org. Chem. 1991, 56, 513
-
(1991)
J. Org. Chem.
, vol.56
, pp. 513
-
-
Kuehne, M.E.1
Matson, P.A.2
Bornmann, W.G.3
-
13
-
-
0027077957
-
-
Magnus, P., Mendoza, J. S., Stamford, A., Ladlow, M., and Willis, P. J. Am. Chem. Soc. 1992, 114, 10232
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 10232
-
-
Magnus, P.1
Mendoza, J.S.2
Stamford, A.3
Ladlow, M.4
Willis, P.5
Govek, S.P.6
Overman, L.E.7
-
14
-
-
0035955155
-
-
Asperazine
-
Asperazine: Govek, S. P. and Overman, L. E. J. Am. Chem. Soc. 2001, 123, 9468
-
(2001)
, vol.123
, pp. 9468
-
-
Govek, S.P.1
Overman, L.E.2
-
15
-
-
34447527566
-
-
Govek, S. P. and Overman, L. E. Tetrahedron 2007, 63, 8499 Quadrigemine C: Lebsack, A. D., Link, J. T., Overman, L. E., and Stearns, B. A. J. Am. Chem. Soc. 2002, 124, 9008
-
(2007)
Tetrahedron
, vol.63
, pp. 8499
-
-
Govek, S.P.1
Overman, L.E.2
Lebsack, A.D.3
Link, J.T.4
Overman, L.E.5
Stearns, B.A.6
Kamenecka, T.M.7
Danishefsky, S.J.8
-
16
-
-
0032538764
-
-
Himastatin
-
Himastatin: Kamenecka, T. M. and Danishefsky, S. J. Angew. Chem., Int. Ed. 1998, 37, 2993
-
(1998)
J. Angew. Chem., Int. Ed.
, vol.37
, pp. 2993
-
-
Kamenecka, T.M.1
Danishefsky, S.2
-
17
-
-
0007002833
-
-
Kamenecka, T. M. and Danishefsky, S. J. Angew. Chem., Int. Ed. 1998, 37, 2995
-
(1998)
Angew. Chem., Int. Ed.
, vol.37
, pp. 2995
-
-
Kamenecka, T.M.1
Danishefsky, S.J.2
-
18
-
-
0035808356
-
-
Kamenecka, T. M. and Danishefsky, S. J. Chem. - Eur. J. 2001, 7, 41 Perophoramidine: Fuchs, J. R. and Funk, R. L. J. Am. Chem. Soc. 2004, 126, 5068
-
(2001)
Chem. - Eur. J.
, vol.7
, pp. 41
-
-
Kamenecka, T.M.1
Danishefsky, S.J.2
Fuchs, J.R.3
Funk, R.L.4
Hendrickson, J.B.5
Göschke, R.6
Rees, R.7
-
19
-
-
0000980290
-
-
Chimonanthine
-
Chimonanthine: Hendrickson, J. B., Göschke, R., and Rees, R. Tetrahedron 1964, 20, 565
-
(1964)
Tetrahedron
, vol.20
, pp. 565
-
-
Hendrickson, J.B.1
-
20
-
-
0000243681
-
-
Scott, A. I., McCapra, F., and Hall, E. S. J. Am. Chem. Soc. 1964, 86, 302
-
(1964)
J. Am. Chem. Soc.
, vol.86
, pp. 302
-
-
Scott, A.I.1
McCapra, F.2
Hall, E.S.3
-
22
-
-
34250811388
-
-
Movassaghi, M. and Schmidt, M. A. Angew. Chem., Int. Ed. 2007, 46, 3725
-
(2007)
Angew. Chem., Int. Ed.
, vol.46
, pp. 3725
-
-
Movassaghi, M.1
Schmidt, M.A.2
Ueda, H.3
Satoh, H.4
Matsumoto, K.5
Sugimoto, K.6
Fukuyama, T.7
Tokuyama, H.8
-
23
-
-
70349978074
-
-
Haplophytine
-
Haplophytine: Ueda, H., Satoh, H., Matsumoto, K., Sugimoto, K., Fukuyama, T., and Tokuyama, H. Angew. Chem., Int. Ed. 2009, 48, 7600
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 7600
-
-
Ueda, H.1
Satoh, H.2
Matsumoto, K.3
Sugimoto, K.4
Fukuyama, T.5
Tokuyama, H.6
-
24
-
-
77952577656
-
-
Nicolaou, K. C., Dalby, S. M., Li, S., Suzuki, T., and Chen, D. Y. K. Angew. Chem., Int. Ed. 2009, 41, 7480
-
(2009)
Angew. Chem., Int. Ed.
, vol.41
, pp. 7480
-
-
Nicolaou, K.C.1
Dalby, S.M.2
Li, S.3
Suzuki, T.4
Chen, D.Y.K.5
Yang, J.6
Wu, H.7
Shen, L.8
Qin, Y.9
-
25
-
-
36148935938
-
-
Communesin F
-
Communesin F: Yang, J., Wu, H., Shen, L., and Qin, Y. J. Am. Chem. Soc. 2007, 129, 13794
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 13794
-
-
Yang, J.1
Wu, H.2
Shen, L.3
Qin, Y.4
-
27
-
-
33646721598
-
-
Geiger, W. B., Conn, J. E., and Waksman, S. A. J. Bacteriol. 1944, 48, 531
-
(1944)
J. Bacteriol.
, vol.48
, pp. 531
-
-
Geiger, W.B.1
Conn, J.E.2
Waksman, S.A.3
-
28
-
-
0017190745
-
-
McInnes, A. G., Taylor, A., and Walter, J. A. J. Am. Chem. Soc. 1976, 98, 6741
-
(1976)
J. Am. Chem. Soc.
, vol.98
, pp. 6741
-
-
McInnes, A.G.1
Taylor, A.2
Walter, J.A.3
-
29
-
-
34250794618
-
-
Brewer, D., McInnes, A. G., Smith, D. G., Taylor, A., Walter, J. A., Loosli, H. R., and Kis, Z. L. J. Chem. Soc., Perkin Trans. 1 1978, 10, 1248
-
(1978)
J. Chem. Soc., Perkin Trans. 1
, vol.10
, pp. 1248
-
-
Brewer, D.1
McInnes, A.G.2
Smith, D.G.3
Taylor, A.4
Walter, J.A.5
Loosli, H.R.6
Kis, Z.L.7
-
30
-
-
0020359362
-
-
Kikuchi, T., Kadota, S., Nakamura, K., Nishi, A., Taga, T., Kaji, T., Osaki, K., and Tubaki, K. Chem. Pharm. Bull. 1982, 30, 3846
-
(1982)
Chem. Pharm. Bull.
, vol.30
, pp. 3846
-
-
Kikuchi, T.1
Kadota, S.2
Nakamura, K.3
Nishi, A.4
Taga, T.5
Kaji, T.6
Osaki, K.7
Tubaki, K.8
-
32
-
-
58149159452
-
-
For the isolation of alkaloid 13, see the following conference report
-
For the isolation of alkaloid 13, see the following conference report: Masashi, H., Mitsuyoshi, S., Hiroshi, M., and Yuji, S. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1994, 36, 557
-
(1994)
Tennen Yuki Kagobutsu Toronkai Koen Yoshishu
, vol.36
, pp. 557
-
-
Masashi, H.1
Mitsuyoshi, S.2
Hiroshi, M.3
Yuji, S.4
-
33
-
-
0029095496
-
-
Nakao, Y., Yeung, B. K. S., Yoshida, W. Y., Scheuer, P. J., and Kelly-Borges, M. J. Am. Chem. Soc. 1995, 117, 8271
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 8271
-
-
Nakao, Y.1
Yeung, B.K.S.2
Yoshida, W.Y.3
Scheuer, P.J.4
Kelly-Borges, M.5
-
34
-
-
0029805586
-
-
Yeung, B. K. S., Nakao, Y., Kinnel, R. B., Carney, J. R., Yoshida, W. Y., Scheuer, P. J., and Kelly-Borges, M. J. Org. Chem. 1996, 61, 7168
-
(1996)
J. Org. Chem.
, vol.61
, pp. 7168
-
-
Yeung, B.K.S.1
Nakao, Y.2
Kinnel, R.B.3
Carney, J.R.4
Yoshida, W.Y.5
Scheuer, P.J.6
Kelly-Borges, M.7
-
35
-
-
0043268087
-
-
Nakao, Y., Kuo, J., Yoshida, W. Y., Kelly, M., and Scheuer, P. J. Org. Lett. 2003, 5, 1387
-
(2003)
Org. Lett.
, vol.5
, pp. 1387
-
-
Nakao, Y.1
Kuo, J.2
Yoshida, W.Y.3
Kelly, M.4
Scheuer, P.J.5
-
36
-
-
33750017133
-
-
Li, G.-Y., Li, B.-G., Yang, T., Yan, J.-F., Liu, G.-Y., and Zhang, G.-L. J. Nat. Prod. 2006, 69, 1374
-
(2006)
J. Nat. Prod.
, vol.69
, pp. 1374
-
-
Li, G.-Y.1
Li, B.-G.2
Yang, T.3
Yan, J.-F.4
Liu, G.-Y.5
Zhang, G.-L.6
-
37
-
-
58149175943
-
-
Ding, G., Jiang, L., Guo, L., Chen, X., Zhang, H., and Che, Y. J. Nat. Prod. 2008, 71, 1861
-
(2008)
J. Nat. Prod.
, vol.71
, pp. 1861
-
-
Ding, G.1
Jiang, L.2
Guo, L.3
Chen, X.4
Zhang, H.5
Che, Y.6
-
38
-
-
4444256771
-
-
Takayama, H., Mori, I., Kitajima, M., Aimi, N., and Lajis, N. H. Org. Lett. 2004, 6, 2945
-
(2004)
Org. Lett.
, vol.6
, pp. 2945
-
-
Takayama, H.1
Mori, I.2
Kitajima, M.3
Aimi, N.4
Lajis, N.H.5
-
39
-
-
77952565909
-
-
The relative configuration of psychotetramine is not known, see: M.S. Thesis, Chiba University, Japan
-
The relative configuration of psychotetramine is not known, see: Mori, I. M.S. Thesis, Chiba University, Japan, 2004.
-
(2004)
-
-
Mori, I.1
-
40
-
-
77952578748
-
-
Ph.D. Thesis, Chiba University, Japan
-
Yohei, M. Ph.D. Thesis, Chiba University, Japan, 2008.
-
(2008)
-
-
Yohei, M.1
-
41
-
-
50749136149
-
-
Marsden, S. P., Watson, E. L., and Raw, S. A. Org. Lett. 2008, 10, 2905
-
(2008)
Org. Lett.
, vol.10
, pp. 2905
-
-
Marsden, S.P.1
Watson, E.L.2
Raw, S.A.3
-
42
-
-
58149147187
-
-
Toumi, M., Couty, F., Marrot, J., and Evano, G. Org. Lett. 2008, 10, 5027
-
(2008)
Org. Lett.
, vol.10
, pp. 5027
-
-
Toumi, M.1
Couty, F.2
Marrot, J.3
Evano, G.4
-
44
-
-
38349136002
-
-
For a 16 linear step synthesis of 1 (13.2% overall yield), see
-
For a 16 linear step synthesis of 1 (13.2% overall yield), see: Matsuda, Y., Kitajima, M., and Takayama, H. Org. Lett. 2008, 10, 125
-
(2008)
Org. Lett.
, vol.10
, pp. 125
-
-
Matsuda, Y.1
Kitajima, M.2
Takayama, H.3
-
45
-
-
77949789628
-
-
Takahashi, N., Ito, T., Matsuda, Y., Kogure, N., Kitajima, M., and Takayama, H. Chem. Commun. 2010, 46, 2501
-
(2010)
Chem. Commun.
, vol.46
, pp. 2501
-
-
Takahashi, N.1
Ito, T.2
Matsuda, Y.3
Kogure, N.4
Kitajima, M.5
Takayama, H.6
-
46
-
-
77649098233
-
-
Beaumont, S., Pons, V., Retailleau, P., Dodd, R. H., and Dauban, P. Angew. Chem., Int. Ed. 2010, 49, 1634
-
(2010)
Angew. Chem., Int. Ed.
, vol.49
, pp. 1634
-
-
Beaumont, S.1
Pons, V.2
Retailleau, P.3
Dodd, R.H.4
Dauban, P.5
-
48
-
-
70149111053
-
-
Newhouse, T., Lewis, C. A., and Baran, P. S. J. Am. Chem. Soc. 2009, 131, 6360
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 6360
-
-
Newhouse, T.1
Lewis, C.A.2
Baran, P.S.3
-
49
-
-
1842602924
-
-
Dimerization at carbon has extensive precedent, for example
-
Dimerization at carbon has extensive precedent, for example: Cheek, G. T. and Nelson, R. F. J. Org. Chem. 1978, 43, 1230
-
(1978)
J. Org. Chem.
, vol.43
, pp. 1230
-
-
Cheek, G.T.1
Nelson, R.F.2
-
51
-
-
37049090324
-
-
Shen, X., Lind, J., Eriksen, T. E., and Merényi, G. J. Chem. Soc., Perkin Trans. 2 1990, 597
-
(1990)
J. Chem. Soc., Perkin Trans. 2
, pp. 597
-
-
Shen, X.1
Lind, J.2
Eriksen, T.E.3
Merényi, G.4
-
53
-
-
0036239412
-
-
Verotta, L., Orsini, F., Sbacchi, M., Scheildler, M. A., Amador, T. A., and Elisabetsky, E. Bioorg. Med. Chem. 2002, 10, 2133
-
(2002)
Bioorg. Med. Chem.
, vol.10
, pp. 2133
-
-
Verotta, L.1
Orsini, F.2
Sbacchi, M.3
Scheildler, M.A.4
Amador, T.A.5
Elisabetsky, E.6
-
54
-
-
0037025722
-
-
Ishikawa, H., Takayama, H., and Aimi, N. Tetrahedron Lett. 2002, 43, 5637
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 5637
-
-
Ishikawa, H.1
Takayama, H.2
Aimi, N.3
-
55
-
-
9444279509
-
-
Ishikawa, H., Kitajima, M., and Takayama, H. Heterocycles 2004, 63, 2597
-
(2004)
Heterocycles
, vol.63
, pp. 2597
-
-
Ishikawa, H.1
Kitajima, M.2
Takayama, H.3
-
56
-
-
64849113664
-
-
references cited therein
-
Kim, J., Ashenhurst, J. A., and Movassaghi, M. Science 2009, 324, 238 and references cited therein
-
(2009)
Science
, vol.324
, pp. 238
-
-
Kim, J.1
Ashenhurst, J.A.2
Movassaghi, M.3
-
57
-
-
20444431969
-
-
Baran, P. S., Shenvi, R. A., and Mitsos, C. A. Angew. Chem., Int. Ed. 2005, 44, 3714
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 3714
-
-
Baran, P.S.1
Shenvi, R.A.2
Mitsos, C.A.3
-
59
-
-
75749117406
-
-
Ma, B., Litvinov, D. N., He, L., Banerjee, B., and Castle, S. L. Angew. Chem., Int. Ed. 2009, 121, 6220
-
(2009)
Angew. Chem., Int. Ed.
, vol.121
, pp. 6220
-
-
Ma, B.1
Litvinov, D.N.2
He, L.3
Banerjee, B.4
Castle, S.L.5
-
60
-
-
75749123121
-
-
Feng, Y. and Chen, G. Angew. Chem., Int. Ed. 2010, 49, 958
-
(2010)
Angew. Chem., Int. Ed.
, vol.49
, pp. 958
-
-
Feng, Y.1
Chen, G.2
-
61
-
-
77749273872
-
-
Hu, W., Zhang, F., Xu, Z., Liu, Q., Cui, Y., and Jia, Y. Org. Lett. 2010, 12, 956
-
(2010)
Org. Lett.
, vol.12
, pp. 956
-
-
Hu, W.1
Zhang, F.2
Xu, Z.3
Liu, Q.4
Cui, Y.5
Jia, Y.6
-
62
-
-
77952578349
-
-
The perturbation of pH in a restricted environment, such as an enzyme pocket, is well known; however, the necessity for strong base reduces the likelihood of such a transformation
-
The perturbation of pH in a restricted environment, such as an enzyme pocket, is well known; however, the necessity for strong base reduces the likelihood of such a transformation.
-
-
-
-
65
-
-
0036495579
-
-
Somei has reported a 1% yield for N1-C3 bond formation when N -hydroxymelatonin and indole (10 equiv) were treated with MsCl
-
Somei has reported a 1% yield for N1-C3 bond formation when N -hydroxymelatonin and indole (10 equiv) were treated with MsCl: Hayashi, T., Peng, W., Nakai, Y.-y., Yamada, K., and Somei, M. Heterocycles 2002, 57, 421
-
(2002)
Heterocycles
, vol.57
, pp. 421
-
-
Hayashi, T.1
Peng, W.2
Yamada, K.3
Somei, M.4
-
66
-
-
0004150882
-
-
Wiley-VCH: Weinheim. For the use of cobalt(II) in a related transformation, see: Chem. Lett. 1975, 273
-
Adam, W. and Deutsche, F. Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer; Wiley-VCH: Weinheim, 2000; p 542. For the use of cobalt(II) in a related transformation, see: Nishinaga, A. Chem. Lett. 1975, 273
-
(2000)
Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer
, pp. 542
-
-
Adam, W.1
Deutsche, F.2
Nishinaga, A.3
-
67
-
-
85032069037
-
-
Mori, K., Goto, M., and Sakai, T. Chem. Pharm. Bull. 1985, 33, 4167
-
(1985)
Chem. Pharm. Bull.
, vol.33
, pp. 4167
-
-
Mori, K.1
Goto, M.2
Sakai, T.3
-
68
-
-
77952555598
-
-
2 chlorination, see: ref 14b
-
2 chlorination, see: ref 14b.
-
-
-
-
69
-
-
55949122492
-
-
Movassaghi, M., Schmidt, M. A., and Ashenhurst, J. A. Org. Lett. 2008, 10, 4009
-
(2008)
Org. Lett.
, vol.10
, pp. 4009
-
-
Movassaghi, M.1
Schmidt, M.A.2
Ashenhurst, J.A.3
-
70
-
-
58849128316
-
-
Richter, J. M., Ishihara, Y., Masuda, T., Whitefield, B. W., Llamas, T., Pohjakallio, A., and Baran, P. S. J. Am. Chem. Soc. 2008, 130, 17938
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 17938
-
-
Richter, J.M.1
Ishihara, Y.2
Masuda, T.3
Whitefield, B.W.4
Llamas, T.5
Pohjakallio, A.6
Baran, P.S.7
-
71
-
-
0025817401
-
-
Hugel, G., Royer, D., Sigaut, F., and Lévy, J. J. Org. Chem. 1991, 56, 4631
-
(1991)
J. Org. Chem.
, vol.56
, pp. 4631
-
-
Hugel, G.1
Royer, D.2
Sigaut, F.3
Lévy, J.4
-
73
-
-
0017368205
-
-
Nakagawa, M., Okajima, H., and Hino, T. J. Am. Chem. Soc. 1977, 99, 4424
-
(1977)
J. Am. Chem. Soc.
, vol.99
, pp. 4424
-
-
Nakagawa, M.1
Okajima, H.2
Hino, T.3
-
74
-
-
85022481701
-
-
Moriarty, R. M., Vaid, R. K., and Koser, G. F. Synlett 1990, 365
-
(1990)
Synlett
, pp. 365
-
-
Moriarty, R.M.1
Vaid, R.K.2
Koser, G.F.3
-
76
-
-
0037009958
-
-
Antilla, J. C., Klapars, A., and Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 11684
-
-
Antilla, J.C.1
Klapars, A.2
Buchwald, S.L.3
-
77
-
-
70349769724
-
-
Burns, N. Z., Baran, P. S., and Hoffmann, R. W. Angew. Chem., Int. Ed. 2009, 48, 2854
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 2854
-
-
Burns, N.Z.1
Baran, P.S.2
Hoffmann, R.W.3
-
78
-
-
77952564503
-
3-Substituted-2-(heteroaryl) indoles
-
For introduction of imidazole nucleophiles to haloindolenines
-
For introduction of imidazole nucleophiles to haloindolenines
-
(1985)
Tetrahedron
, vol.59
, pp. 1033
-
-
Renfroe, H.B.1
Bergman, J.2
Engqvist, R.3
Stälhandske, C.4
Wallberg, H.5
He, L.6
Yang, L.7
Castle, S.L.8
-
80
-
-
0037429056
-
-
Anilines
-
Anilines: Bergman, J., Engqvist, R., Stälhandske, C., and Wallberg, H. Tetrahedron 2003, 59, 1033
-
(2003)
Tetrahedron
, vol.59
, pp. 1033
-
-
Bergman, J.1
-
81
-
-
33646453051
-
-
Imidazoles
-
Imidazoles: He, L., Yang, L., and Castle, S. L. Org. Lett. 2006, 8, 1165
-
(2006)
Org. Lett.
, vol.8
, pp. 1165
-
-
He, L.1
Yang, L.2
Castle, S.L.3
-
82
-
-
76149144042
-
-
Ma, B., Banerjee, B., Litvinov, D. N., He, L., and Castle, S. L. J. Am. Chem. Soc. 2010, 132, 1159
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 1159
-
-
Ma, B.1
Banerjee, B.2
Litvinov, D.N.3
He, L.4
Castle, S.L.5
-
83
-
-
0034622296
-
-
Sheppeckll, J. E., Kar, H., and Hong, H. Tetrahedron Lett. 2000, 41, 5329
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 5329
-
-
Sheppeckll, J.E.1
Kar, H.2
Hong, H.3
-
84
-
-
33751317736
-
-
For recent reviews on protecting group free synthesis, see
-
For recent reviews on protecting group free synthesis, see: Hoffmann, R. W. Synthesis 2006, 3531
-
(2006)
Synthesis
, pp. 3531
-
-
Hoffmann, R.W.1
-
86
-
-
77952571775
-
-
13C, and HSQC NMR experiments support this structural assignment)
-
13C, and HSQC NMR experiments support this structural assignment).
-
-
-
-
87
-
-
0014405161
-
-
Ohno, M., Spande, T., and Witkop, B. J. Am. Chem. Soc. 1968, 90, 6521
-
(1968)
J. Am. Chem. Soc.
, vol.90
, pp. 6521
-
-
Ohno, M.1
Spande, T.2
Witkop, B.3
-
88
-
-
77952564355
-
-
See Figure 11 for excellent diastereoselectivities in the oxidative coupling reaction
-
See Figure 11 for excellent diastereoselectivities in the oxidative coupling reaction.
-
-
-
-
89
-
-
77952566866
-
-
In the case of acid-mediated ring closure, the more stabile endo diastereomer is obtained due to the reversibility of product formation. See ref 38b for further explanation
-
In the case of acid-mediated ring closure, the more stabile endo diastereomer is obtained due to the reversibility of product formation. See ref 38b for further explanation.
-
-
-
-
90
-
-
0028566539
-
-
Marsden, S. P., Depew, K. M., and Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 11143
-
-
Marsden, S.P.1
Depew, K.M.2
Danishefsky, S.J.3
-
91
-
-
38349106245
-
-
López, C. S., Pérez-Balado, C., Rodríguez- Graña, P., and de Lera, A. R. Org. Lett. 2008, 10, 77
-
(2008)
Org. Lett.
, vol.10
, pp. 77
-
-
López, C.S.1
Pérez-Balado, C.2
Rodríguez-Graña, P.3
De Lera, A.R.4
-
92
-
-
0033616097
-
-
Depew, K. M., Marsden, S. P., Zatorska, D., Zatorski, A., Bornmann, W. G., and Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 11953
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 11953
-
-
Depew, K.M.1
Marsden, S.P.2
Zatorska, D.3
Zatorski, A.4
Bornmann, W.G.5
Danishefsky, S.J.6
-
94
-
-
77952567629
-
-
The postulated difference between torsional strains of the transition states, as compared to that of the products, is suggested to arise from differing hybridization of the carbamate nitrogen lone pair. See ref 38b for further discussion
-
The postulated difference between torsional strains of the transition states, as compared to that of the products, is suggested to arise from differing hybridization of the carbamate nitrogen lone pair. See ref 38b for further discussion.
-
-
-
-
95
-
-
0034624605
-
-
Kawahara, M., Nishida, A., and Nakagawa, M. Org. Lett. 2000, 2, 675
-
(2000)
Org. Lett.
, vol.2
, pp. 675
-
-
Kawahara, M.1
Nishida, A.2
Nakagawa, M.3
-
96
-
-
26844527594
-
-
May, J. P., Fournier, P., Pellicelli, J., Patrick, B. O., and Perrin, D. M. J. Org. Chem. 2005, 70, 8424
-
(2005)
J. Org. Chem.
, vol.70
, pp. 8424
-
-
May, J.P.1
Fournier, P.2
Pellicelli, J.3
Patrick, B.O.4
Perrin, D.M.5
-
97
-
-
33846552386
-
-
May, J. P., Patrick, B. O., and Perrin, D. M. Synlett 2006, 3403
-
(2006)
Synlett
, pp. 3403
-
-
May, J.P.1
Patrick, B.O.2
Perrin, D.M.3
-
98
-
-
34547406299
-
-
González-Vera, J. A., García-López, M. T., and Herranz, R. Tetrahedron 2007, 63, 9229
-
(2007)
Tetrahedron
, vol.63
, pp. 9229
-
-
González-Vera, J.A.1
García-López, M.T.2
Herranz, R.3
-
99
-
-
77952564077
-
-
It is also instructive to compare the high diastereoselectivity in production of 102a - c with the poor selectivity for formation of compound 8 in ref 40c
-
It is also instructive to compare the high diastereoselectivity in production of 102a - c with the poor selectivity for formation of compound 8 in ref 40c.
-
-
-
-
100
-
-
0029787938
-
-
For reversible interactions of phenyl nitreniums with arenes, see
-
For reversible interactions of phenyl nitreniums with arenes, see: Robbins, R. J., Laman, D. M., and Falvey, D. E. J. Am. Chem. Soc. 1996, 118, 8127
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 8127
-
-
Robbins, R.J.1
Laman, D.M.2
Falvey, D.E.3
-
102
-
-
0037051648
-
-
For recent studies on reversible reactions of electrophiles with olefins
-
Chiapperino, D., Mcllroy, S., and Falvey, D. E. J. Am. Chem. Soc. 2002, 124, 3567 For recent studies on reversible reactions of electrophiles with olefins
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 3567
-
-
Chiapperino, D.1
McLlroy, S.2
Falvey, D.E.3
Denmark, S.E.4
Collins, W.R.5
Cullen, M.D.6
-
103
-
-
69949112440
-
-
see
-
see: Denmark, S. E., Collins, W. R., and Cullen, M. D. J. Am. Chem. Soc. 2009, 131, 3490
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 3490
-
-
Denmark, S.E.1
Collins, W.R.2
Cullen, M.D.3
-
104
-
-
77950341605
-
-
Denmark, S. E., Burk, M. T., and Hoover, A. J. J. Am. Chem. Soc. 2010, 132, 1232
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 1232
-
-
Denmark, S.E.1
Burk, M.T.2
Hoover, A.J.3
-
106
-
-
0037576109
-
-
Gassman, P. G., Campbell, G. A., and Frederick, R. C. J. Am. Chem. Soc. 1972, 94, 3884
-
(1972)
J. Am. Chem. Soc.
, vol.94
, pp. 3884
-
-
Gassman, P.G.1
Campbell, G.A.2
Frederick, R.C.3
-
108
-
-
33845375138
-
-
Leyva, E., Platz, M. S., Persy, G., and Wirz, J. J. Am. Chem. Soc. 1986, 108, 3783
-
(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 3783
-
-
Leyva, E.1
Platz, M.S.2
Persy, G.3
Wirz, J.4
-
109
-
-
0030006665
-
-
McClelland, R. A., Kahley, M. J., Davidse, P. A., and Hadzialic, G. J. Am. Chem. Soc. 1996, 118, 4794
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 4794
-
-
McClelland, R.A.1
Kahley, M.J.2
Davidse, P.A.3
Hadzialic, G.4
-
110
-
-
0001151962
-
-
Watt, D. S., Kawada, K., Leyva, E., and Platz, M. S. Tetrahedron Lett. 1989, 30, 899
-
(1989)
Tetrahedron Lett.
, vol.30
, pp. 899
-
-
Watt, D.S.1
Kawada, K.2
Leyva, E.3
Platz, M.S.4
-
111
-
-
0032692090
-
-
Ding, Y., Padias, A. B., and Hall, H. K., Jr. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 2569
-
(1999)
J. Polym. Sci., Part A: Polym. Chem.
, vol.37
, pp. 2569
-
-
Ding, Y.1
Padias, A.B.2
Hall Jr., H.K.3
-
112
-
-
0037778963
-
-
Wojciechowski, P. M., Zierkiewicz, W., Michalska, D., and Hobza, P. J. Chem. Phys. 2003, 118, 10900
-
(2003)
J. Chem. Phys.
, vol.118
, pp. 10900
-
-
Wojciechowski, P.M.1
Zierkiewicz, W.2
Michalska, D.3
Hobza, P.4
-
116
-
-
0001447926
-
-
N2) between arenes and activated esters of N -phenylhydroxylamine, see
-
N2) between arenes and activated esters of N -phenylhydroxylamine, see: Shudo, K., Ohta, T., and Okamoto, T. J. Am. Chem. Soc. 1981, 103, 645
-
(1981)
J. Am. Chem. Soc.
, vol.103
, pp. 645
-
-
Shudo, K.1
Ohta, T.2
Okamoto, T.3
-
117
-
-
37049071804
-
-
Hamel, P., Girard, Y., and Atkinson, J. G. J. Chem. Soc., Chem. Commun. 1989, 63
-
(1989)
J. Chem. Soc., Chem. Commun.
, pp. 63
-
-
Hamel, P.1
Girard, Y.2
Atkinson, J.G.3
-
118
-
-
0024819867
-
-
Novak, M., Martin, K. A., and Heinrich, J. L. J. Org. Chem. 1989, 54, 5430
-
(1989)
J. Org. Chem.
, vol.54
, pp. 5430
-
-
Novak, M.1
Martin, K.A.2
Heinrich, J.L.3
-
119
-
-
0000477567
-
-
Helmick, J. S., Martin, K. A., Heinrich, J. L., and Novak, M. J. Am. Chem. Soc. 1991, 113, 3459
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 3459
-
-
Helmick, J.S.1
Martin, K.A.2
Heinrich, J.L.3
Novak, M.4
-
120
-
-
0027717195
-
-
Novak, M., Rangappa, K. S., and Manitsas, R. K. J. Org. Chem. 1993, 58, 7813
-
(1993)
J. Org. Chem.
, vol.58
, pp. 7813
-
-
Novak, M.1
Rangappa, K.S.2
Manitsas, R.K.3
-
121
-
-
33947408403
-
-
13C NMR experiments did not allow observation of changes indicative of π-stacking
-
13C NMR experiments did not allow observation of changes indicative of π-stacking.
-
(2007)
Acc. Chem. Res.
, vol.40
, pp. 151
-
-
Crich, D.1
Bannerjee, A.2
-
122
-
-
33745506850
-
-
Mathew, J. S., Klussmann, M., Iwamura, H., Valera, F., Futran, A., Emanuelsson, E. A. C., and Blackmond, D. G. J. Org. Chem. 2006, 71, 4711
-
(2006)
J. Org. Chem.
, vol.71
, pp. 4711
-
-
Mathew, J.S.1
Klussmann, M.2
Iwamura, H.3
Valera, F.4
Futran, A.5
Emanuelsson, E.A.C.6
Blackmond, D.G.7
-
125
-
-
77952578491
-
-
The increased yield for p -iodoaniline to afford 63 (27%) and 47% recovered 33 with NCS (unoptimized) suggests that substrates can be optimized when standard conditions fail (Scheme 6)
-
The increased yield for p -iodoaniline to afford 63 (27%) and 47% recovered 33 with NCS (unoptimized) suggests that substrates can be optimized when standard conditions fail (Scheme 6).
-
-
-
-
126
-
-
33744870975
-
-
Larock, R. C., Yum, E. K., and Refvik, M. D. J. Org. Chem. 1998, 63, 7652
-
(1998)
J. Org. Chem.
, vol.63
, pp. 7652
-
-
Larock, R.C.1
Yum, E.K.2
Refvik, M.D.3
-
129
-
-
0034712156
-
-
Wolfe, J. P., Tomori, H., Sadighi, J. P., Yin, J., and Buchwald, S. L. J. Org. Chem. 2000, 65, 1158
-
(2000)
J. Org. Chem.
, vol.65
, pp. 1158
-
-
Wolfe, J.P.1
Tomori, H.2
Sadighi, J.P.3
Yin, J.4
Buchwald, S.L.5
-
131
-
-
46849092613
-
-
Altman, R. A., Anderson, K. W., and Buchwald, S. L. J. Org. Chem. 2008, 73, 5167
-
(2008)
J. Org. Chem.
, vol.73
, pp. 5167
-
-
Altman, R.A.1
Anderson, K.W.2
Buchwald, S.L.3
-
132
-
-
55949121639
-
-
Coste, A., Toumi, M., Wright, K., Razafimahaléo, V., Couty, F., Marrot, J., and Evano, G. Org. Lett. 2008, 10, 3841
-
(2008)
Org. Lett.
, vol.10
, pp. 3841
-
-
Coste, A.1
Toumi, M.2
Wright, K.3
Razafimahaléo, V.4
Couty, F.5
Marrot, J.6
Evano, G.7
-
133
-
-
77952577918
-
-
The methyl carbamate was available in quantitative yield from the commercial 7-bromotryptamine, whose preparation can be found in ref 13a. An alternative preparation may be found in the Supporting Information
-
The methyl carbamate was available in quantitative yield from the commercial 7-bromotryptamine, whose preparation can be found in ref 13a. An alternative preparation may be found in the Supporting Information.
-
-
-
-
134
-
-
77952578208
-
-
Kapakahi is the Hawaiian word for twisted
-
Kapakahi is the Hawaiian word for twisted.
-
-
-
-
135
-
-
77952577217
-
-
Varying the substrate or oxidant led to unproductive oxidation, double addition, or no reaction at all
-
Varying the substrate or oxidant led to unproductive oxidation, double addition, or no reaction at all.
-
-
-
-
136
-
-
33846304654
-
-
Chaetominine isolation: Jiao, R. H., Xu, S., Liu, J. Y., Ge, H. M., Ding, H., Xu, C., Zhu, H. L., and Tan, R. X. Org. Lett. 2006, 8, 5709
-
(2006)
Org. Lett.
, vol.8
, pp. 5709
-
-
Jiao, R.H.1
Xu, S.2
Liu, J.Y.3
Ge, H.M.4
Ding, H.5
Xu, C.6
Zhu, H.L.7
Tan, R.X.8
Snider, B.B.9
Wu, X.10
-
137
-
-
36348961992
-
-
Synthesis of chaetominine
-
Synthesis of chaetominine: Snider, B. B. and Wu, X. Org. Lett. 2007, 9, 4913
-
(2007)
Org. Lett.
, vol.9
, pp. 4913
-
-
Snider, B.B.1
Wu, X.2
-
138
-
-
58149147187
-
-
Malgesini, B., Forte, B., Toumi, M., Couty, F., Marrot, J., and Evano, G. Org. Lett. 2008, 10, 5027
-
(2008)
Org. Lett.
, vol.10
, pp. 5027
-
-
Malgesini, B.1
Forte, B.2
Toumi, M.3
Couty, F.4
Marrot, J.5
Evano, G.6
-
139
-
-
68349101069
-
-
Borghi, D., Quartieri, F., Gennari, C., and Papeo, G. Chem. - Eur. J. 2009, 15, 7922
-
(2009)
Chem. - Eur. J.
, vol.15
, pp. 7922
-
-
Borghi, D.1
Quartieri, F.2
Gennari, C.3
Papeo, G.4
-
140
-
-
70449367341
-
-
Coste, A., Karthikeyan, G., Couty, F., and Evano, G. Synthesis 2009, 17, 2927
-
(2009)
Synthesis
, vol.17
, pp. 2927
-
-
Coste, A.1
Karthikeyan, G.2
Couty, F.3
Evano, G.4
-
141
-
-
84985516415
-
-
Schöllkopf, U., Groth, U., and Deng, C. Angew. Chem., Int. Ed. Engl. 1981, 20, 798-799
-
(1981)
Angew. Chem., Int. Ed. Engl.
, vol.20
, pp. 798-799
-
-
Schöllkopf, U.1
Groth, U.2
Deng, C.3
-
142
-
-
34548524315
-
-
Ma, J., Yin, W., Zhou, H., and Cook, J. M. Org. Lett. 2007, 9, 3491
-
(2007)
Org. Lett.
, vol.9
, pp. 3491
-
-
Ma, J.1
Yin, W.2
Zhou, H.3
Cook, J.M.4
-
143
-
-
31144432900
-
-
Zhou, H., Liao, X., Yin, W., Ma, J., and Cook, J. M. J. Org. Chem. 2006, 71, 251
-
(2006)
J. Org. Chem.
, vol.71
, pp. 251
-
-
Zhou, H.1
Liao, X.2
Yin, W.3
Ma, J.4
Cook, J.M.5
-
144
-
-
18744399313
-
-
Yu, J., Wearing, X. Z., and Cook, J. M. J. Org. Chem. 2005, 70, 3963
-
(2005)
J. Org. Chem.
, vol.70
, pp. 3963
-
-
Yu, J.1
Wearing, X.Z.2
Cook, J.M.3
-
145
-
-
0842306887
-
-
Zhou, H., Liao, K., and Cook, J. M. Org. Lett. 2004, 6, 249
-
(2004)
Org. Lett.
, vol.6
, pp. 249
-
-
Zhou, H.1
Liao, K.2
Cook, J.M.3
-
146
-
-
0037015424
-
-
Liu, X., Deschamp, J. R., and Cook, J. R. Org. Lett. 2002, 4, 3339
-
(2002)
Org. Lett.
, vol.4
, pp. 3339
-
-
Liu, X.1
Deschamp, J.R.2
Cook, J.R.3
-
147
-
-
0035967767
-
-
Ma, C., Liu, X., Li, X., Flippen-Anderson, J., Yu, S., and Cook, J. M. J. Org. Chem. 2001, 55, 4525
-
(2001)
J. Org. Chem.
, vol.55
, pp. 4525
-
-
Ma, C.1
Liu, X.2
Li, X.3
Flippen-Anderson, J.4
Yu, S.5
Cook, J.M.6
-
152
-
-
0037733052
-
-
IJsselstijn, M., Kaiser, J., van Delft, F. L., Schoemaker, H. E., and Rutjes, F. P. J. T. Amino Acids 2003, 24, 263
-
(2003)
Amino Acids
, vol.24
, pp. 263
-
-
Ijsselstijn, M.1
Kaiser, J.2
Van Delft, F.L.3
Schoemaker, H.E.4
Rutjes, F.P.J.T.5
-
153
-
-
33845553316
-
-
Boggs, N. T., Bruton, H. D., Craig, D. H., Helpern, J. A., Marsh, H. C., Pegram, M. D., Vandenbergh, D. J., Koehler, K. A., and Hiskey, R. G. J. Org. Chem. 1982, 47, 1812
-
(1982)
J. Org. Chem.
, vol.47
, pp. 1812
-
-
Boggs, N.T.1
Bruton, H.D.2
Craig, D.H.3
Helpern, J.A.4
Marsh, H.C.5
Pegram, M.D.6
Vandenbergh, D.J.7
Koehler, K.A.8
Hiskey, R.G.9
-
154
-
-
70450187429
-
-
For the first example of a macrocyclic Larock cyclization, see: Garfunkle, J., Kimball, F. S., Kimball, F. S., Trzupek, J. D., Takizawa, S., Shimamura, H., Tomishima, M., and Boger, D. L. J. Am. Chem. Soc. 2009, 131, 16036.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 16036
-
-
Garfunkle, J.1
Kimball, F.S.2
Kimball, F.S.3
Trzupek, J.D.4
Takizawa, S.5
Shimamura, H.6
Tomishima, M.7
Boger, D.L.8
-
155
-
-
77952559434
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-
Although no base is added, either DMF or trace dimethylamine may act as a base in this peptide coupling reaction
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Although no base is added, either DMF or trace dimethylamine may act as a base in this peptide coupling reaction.
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156
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77952558754
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f values of 0.58 and 0.43, respectively (4:1 EtOAc/hexanes)
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f values of 0.58 and 0.43, respectively (4:1 EtOAc/hexanes).
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159
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77952564502
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1H NMR to that of the natural source, please see ref 13b. For HMQC, HMBC, and ROESY NMR data for kapakahine F (2), please see the Supporting Information
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1H NMR to that of the natural source, please see ref 13b. For HMQC, HMBC, and ROESY NMR data for kapakahine F (2), please see the Supporting Information.
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160
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77952563948
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Assays performed by Bristol-Myers Squibb
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Assays performed by Bristol-Myers Squibb.
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-
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161
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77952559041
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Assays performed by the NCI
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Assays performed by the NCI.
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-
162
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33947602410
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-
Baran, P. S., Maimone, T. J., and Richter, J. M. Nature 2007, 446, 404
-
(2007)
Nature
, vol.446
, pp. 404
-
-
Baran, P.S.1
Maimone, T.J.2
Richter, J.M.3
-
163
-
-
66449129817
-
-
Shenvi, R. A., OMalley, D. P., and Baran, P. S. Acc. Chem. Res. 2009, 42, 530
-
(2009)
Acc. Chem. Res.
, vol.42
, pp. 530
-
-
Shenvi, R.A.1
Omalley, D.P.2
Baran, P.S.3
-
165
-
-
77951870400
-
-
During the review of this manuscript, a synthesis of kapakahine F was reported that proceeded in 19 linear steps and 6.8% overall yield (23 mg produced) from tryptophan:, DOI: 10.1021/ol100672z (published ASAP online Mar 26, 2010)
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During the review of this manuscript, a synthesis of kapakahine F was reported that proceeded in 19 linear steps and 6.8% overall yield (23 mg produced) from tryptophan: Espejo, V. R. and Rainier, J. D. Org. Lett. 2010, 12, DOI: 10.1021/ol100672z (published ASAP online Mar 26, 2010).
-
(2010)
Org. Lett.
, vol.12
-
-
Espejo, V.R.1
Rainier, J.D.2
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