-
1
-
-
0031253587
-
-
Ostlind, D. A.; Felcetto, T.; Misura, A.; Ondeyka, J.; Smith, S.; Goetz, M.; Shoop, W.; Mickle, W. Med. Vet. Entomol. 1997, 11, 407-408.
-
(1997)
Med. Vet. Entomol
, vol.11
, pp. 407-408
-
-
Ostlind, D.A.1
Felcetto, T.2
Misura, A.3
Ondeyka, J.4
Smith, S.5
Goetz, M.6
Shoop, W.7
Mickle, W.8
-
2
-
-
0030839562
-
-
Ondeyka, J. G.; Helms, G. L.; Hensens, O. D.; Goetz, M. A.; Zink, D. L.; Tsipouras, A.; Shoop, W. L.; Slayton, L.; Dombrowski, A. W.; Polishook, J. D.; Ostlind, D. A.; Tsou, N. N.; Ball, R. G.; Singh, S. B. J. Am. Chem. Soc. 1997, 119, 8809-8816.
-
(1997)
J. Am. Chem. Soc
, vol.119
, pp. 8809-8816
-
-
Ondeyka, J.G.1
Helms, G.L.2
Hensens, O.D.3
Goetz, M.A.4
Zink, D.L.5
Tsipouras, A.6
Shoop, W.L.7
Slayton, L.8
Dombrowski, A.W.9
Polishook, J.D.10
Ostlind, D.A.11
Tsou, N.N.12
Ball, R.G.13
Singh, S.B.14
-
3
-
-
0037129410
-
-
Chakravarty, P. K.; Tyagarajan, S.; Shih, T. L.; Salva, S.; Snedden, C.; Wyvratt, M. J.; Fisher, M. H.; Meinke, P. T. Org. Lett. 2002, 4, 1291-1294.
-
(2002)
Org. Lett
, vol.4
, pp. 1291-1294
-
-
Chakravarty, P.K.1
Tyagarajan, S.2
Shih, T.L.3
Salva, S.4
Snedden, C.5
Wyvratt, M.J.6
Fisher, M.H.7
Meinke, P.T.8
-
4
-
-
18044399538
-
-
Berger, R.; Shoop, W. L.; Pivnichny, J. V.; Warmke, L. M.; Zakson-Aiken, M.; Owens, K. A.; deMontigny, P.; Schmatz, D. M.; Wyvratt, M. J.; Fisher, M. H.; Meinke, P. T.; Colletti, S. L. Org. Lett. 2001, 3, 3715-3718.
-
(2001)
Org. Lett
, vol.3
, pp. 3715-3718
-
-
Berger, R.1
Shoop, W.L.2
Pivnichny, J.V.3
Warmke, L.M.4
Zakson-Aiken, M.5
Owens, K.A.6
deMontigny, P.7
Schmatz, D.M.8
Wyvratt, M.J.9
Fisher, M.H.10
Meinke, P.T.11
Colletti, S.L.12
-
5
-
-
34250854598
-
-
Smith, A. B., III; Davulcu, A. H.; Cho, Y. S.; Ohmoto, K.; Kürti, L.; Ishiyama, H. J. Org. Chem. 2007, 72, 4596-4610.
-
(2007)
J. Org. Chem
, vol.72
, pp. 4596-4610
-
-
Smith III, A.B.1
Davulcu, A.H.2
Cho, Y.S.3
Ohmoto, K.4
Kürti, L.5
Ishiyama, H.6
-
6
-
-
0001150685
-
-
Smith, A. B., III; Visnick, M.; Haseltine, J. N.; Sprengeler, P. A. Tetrahedron 1986, 42, 2957-2969.
-
(1986)
Tetrahedron
, vol.42
, pp. 2957-2969
-
-
Smith III, A.B.1
Visnick, M.2
Haseltine, J.N.3
Sprengeler, P.A.4
-
9
-
-
0034669287
-
-
Smith, A. B., III; Kanoh, N.; Ishiyama, H.; Hartz, R. A. J. Am. Chem. Soc. 2000, 122, 11254-11255.
-
(2000)
J. Am. Chem. Soc
, vol.122
, pp. 11254-11255
-
-
Smith III, A.B.1
Kanoh, N.2
Ishiyama, H.3
Hartz, R.A.4
-
10
-
-
0038682516
-
-
Smith, A. B.; Kanoh, N.; Ishiyama, H.; Minakawa, N.; Rainier, J. D.; Hartz, R. A.; Cho, Y. S.; Cui, H.; Moser, W. H. J. Am. Chem. Soc. 2003, 125, 8228-8237.
-
(2003)
J. Am. Chem. Soc
, vol.125
, pp. 8228-8237
-
-
Smith, A.B.1
Kanoh, N.2
Ishiyama, H.3
Minakawa, N.4
Rainier, J.D.5
Hartz, R.A.6
Cho, Y.S.7
Cui, H.8
Moser, W.H.9
-
12
-
-
0000802361
-
-
Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652.
-
(1997)
Org. React
, vol.50
, pp. 1-652
-
-
Farina, V.1
Krishnamurthy, V.2
Scott, W.J.3
-
13
-
-
33744738548
-
-
Smith, A. B., III; Kürti, L.; Davulcu, A. H. Org. Lett. 2006, 8, 2167-2170.
-
(2006)
Org. Lett
, vol.8
, pp. 2167-2170
-
-
Smith III, A.B.1
Kürti, L.2
Davulcu, A.H.3
-
14
-
-
0028070649
-
-
Black, D. S. C.; Bowyer, M. C.; Catalano, M. M.; Ivory, A. J.; Keller, P. A.; Kumar, N.; Nugent, S. J. Tetrahedron 1994, 50, 10497-10508.
-
(1994)
Tetrahedron
, vol.50
, pp. 10497-10508
-
-
Black, D.S.C.1
Bowyer, M.C.2
Catalano, M.M.3
Ivory, A.J.4
Keller, P.A.5
Kumar, N.6
Nugent, S.J.7
-
16
-
-
34250887578
-
-
Dankwardt and co-workers also examined the effect of the ring size on the mode of ring closure and therefore prepared an N-acryloyl-8- bromotetrahydroquinoline derivative upon Heck cyclization, and the ratio of the 5-exo-trig versus the 6-endo-trig products was reversed, favoring the former mode of cyclization. The authors concluded that the 6-endo-trig cyclization mode is only favored in systems (i.e, indoles and indolines) wherein the strain of the transition state would severely suppress the 5-exo- trig mode of ring closure
-
Dankwardt and co-workers also examined the effect of the ring size on the mode of ring closure and therefore prepared an N-acryloyl-8- bromotetrahydroquinoline derivative upon Heck cyclization, and the ratio of the 5-exo-trig versus the 6-endo-trig products was reversed, favoring the former mode of cyclization. The authors concluded that the 6-endo-trig cyclization mode is only favored in systems (i.e., indoles and indolines) wherein the strain of the transition state would severely suppress the 5-exo- trig mode of ring closure.
-
-
-
-
17
-
-
0030845067
-
-
For a few examples of radical or Pd-catalyzed cyclization of N-allyl-7-bromoindoles (Scheme 4), see: (a) Dobbs, A. P.; Jones, K.; Veal, K. T. Tetrahedron Lett. 1997, 38, 5379-5382.
-
For a few examples of radical or Pd-catalyzed cyclization of N-allyl-7-bromoindoles (Scheme 4), see: (a) Dobbs, A. P.; Jones, K.; Veal, K. T. Tetrahedron Lett. 1997, 38, 5379-5382.
-
-
-
-
18
-
-
0026663302
-
-
(b) Black, D. S. C.; Keller, P. A.; Kumar, N. Tetrahedron 1992, 48, 7601-7608.
-
(1992)
Tetrahedron
, vol.48
, pp. 7601-7608
-
-
Black, D.S.C.1
Keller, P.A.2
Kumar, N.3
-
19
-
-
34250870778
-
-
Intramolecular reactions between carbon-centered radicals and olefins prefer to proceed via a kinetic 5-exo-trig cyclization for stereoelectronic reasons. However, in the case of compound 17, only the corresponding 6-endo-trig cyclization product 19 was obtained along with some reduced product 20. Similar observations were obtained with the Pd-catalyzed cyclization of indole 21. The authors14 attributed the observed selectivity favoring the 6-endo-trig cyclization to the considerable strain and distortion in the transition state leading to the five-membered 1,7-annulated products, Chemical Equation Presented
-
14 attributed the observed selectivity favoring the 6-endo-trig cyclization to the considerable strain and distortion in the transition state leading to the five-membered 1,7-annulated products. (Chemical Equation Presented)
-
-
-
-
20
-
-
34250852967
-
-
See Supporting Information
-
See Supporting Information.
-
-
-
-
26
-
-
0000010274
-
-
Trost, B. M, Fleming, I, Eds, Pergamon: Oxford
-
Davis, D. R.; Garratt, P. J. In Comprehensive Organic Syntheses; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 795-863.
-
(1991)
Comprehensive Organic Syntheses
, vol.2
, pp. 795-863
-
-
Davis, D.R.1
Garratt, P.J.2
-
29
-
-
0027131604
-
-
van Wijngaarden, I.; Hamminga, D.; van Hes, R.; Standaar, P. J.; Tipker, J.; Tulp, M. T. M.; Mol, F.; Olivier, B.; de Jonge, A. J. Med. Chem. 1993, 36, 3693-3699.
-
(1993)
J. Med. Chem
, vol.36
, pp. 3693-3699
-
-
van Wijngaarden, I.1
Hamminga, D.2
van Hes, R.3
Standaar, P.J.4
Tipker, J.5
Tulp, M.T.M.6
Mol, F.7
Olivier, B.8
de Jonge, A.9
-
30
-
-
33845552648
-
-
O'Connor, J. M.; Stallman, B. J.; Clark, W. G.; Shu, A. Y. L.; Spada, R. E.; Stevenson, T. M.; Dieck, H. A. J. Org. Chem. 1983, 48, 807-809.
-
(1983)
J. Org. Chem
, vol.48
, pp. 807-809
-
-
O'Connor, J.M.1
Stallman, B.J.2
Clark, W.G.3
Shu, A.Y.L.4
Spada, R.E.5
Stevenson, T.M.6
Dieck, H.A.7
-
31
-
-
34250889451
-
-
Generally, absolute ethanol at reflux is sufficient for the preparation of hydrazones; however, even after 12 h at reflux, we observed less than 5% of hydrazone 32, accompanied by significant decomposition of the hydrazine. Acetic acid was therefore added to catalyze the transformation.
-
Generally, absolute ethanol at reflux is sufficient for the preparation of hydrazones; however, even after 12 h at reflux, we observed less than 5% of hydrazone 32, accompanied by significant decomposition of the hydrazine. Acetic acid was therefore added to catalyze the transformation.
-
-
-
-
32
-
-
0033997284
-
-
Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370.
-
(2000)
J. Am. Chem. Soc
, vol.122
, pp. 1360-1370
-
-
Fox, J.M.1
Huang, X.2
Chieffi, A.3
Buchwald, S.L.4
-
36
-
-
0141542721
-
-
Diep, V.; Dannenberg, J. J.; Franck, R. W. J. Org. Chem. 2003, 68, 7907-7910.
-
(2003)
J. Org. Chem
, vol.68
, pp. 7907-7910
-
-
Diep, V.1
Dannenberg, J.J.2
Franck, R.W.3
-
37
-
-
0026500938
-
-
Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W. Tetrahedron Lett. 1992, 33, 917-918.
-
(1992)
Tetrahedron Lett
, vol.33
, pp. 917-918
-
-
Johnson, C.R.1
Adams, J.P.2
Braun, M.P.3
Senanayake, C.B.W.4
-
38
-
-
34250806627
-
-
The reaction was also found to be very sensitive to the anhydrous state of the NMP; that is, not sufficiently dried NMP caused the arylstannane 35 to undergo significant protodestannylation at the reaction temperature. The protodestannylation was found to be much faster than the cross-coupling; in some cases, no coupling product (40) was observed.
-
The reaction was also found to be very sensitive to the anhydrous state of the NMP; that is, not sufficiently dried NMP caused the arylstannane 35 to undergo significant protodestannylation at the reaction temperature. The protodestannylation was found to be much faster than the cross-coupling; in some cases, no coupling product (40) was observed.
-
-
-
-
39
-
-
0010521593
-
-
A survey of the literature revealed that this transformation might prove quite challenging since a mixture of 1,2- and 1,4-reduction products had been reported for many combination of enones and reducing agents: (a) Fortunato, J. M, Ganem, B. J. Org. Chem. 1976, 41, 2194-2200
-
A survey of the literature revealed that this transformation might prove quite challenging since a mixture of 1,2- and 1,4-reduction products had been reported for many combination of enones and reducing agents: (a) Fortunato, J. M.; Ganem, B. J. Org. Chem. 1976, 41, 2194-2200.
-
-
-
-
40
-
-
33845554778
-
-
(b) Kowalski, C. J.; Weber, A. E.; Fields, K. W. J. Org. Chem. 1982, 47, 5088-5093.
-
(1982)
J. Org. Chem
, vol.47
, pp. 5088-5093
-
-
Kowalski, C.J.1
Weber, A.E.2
Fields, K.W.3
-
45
-
-
12344275854
-
-
Willis, M. C.; Brace, G. N.; Holmes, I. P. Angew. Chem., Int. Ed. 2005, 44, 403-406.
-
(2005)
Angew. Chem., Int. Ed
, vol.44
, pp. 403-406
-
-
Willis, M.C.1
Brace, G.N.2
Holmes, I.P.3
-
49
-
-
37049091241
-
-
Lott, R. S.; Chauhan, V. S.; Stammer, C. H. J. Chem. Soc., Chem. Commun. 1979, 495-496.
-
(1979)
J. Chem. Soc., Chem. Commun
, pp. 495-496
-
-
Lott, R.S.1
Chauhan, V.S.2
Stammer, C.H.3
-
50
-
-
34250903652
-
-
Further increase in catalyst and ligand loadings did not result in higher yields of tetracyclic indole 45
-
Further increase in catalyst and ligand loadings did not result in higher yields of tetracyclic indole 45.
-
-
-
-
51
-
-
0034999411
-
-
Xie, W.; Peng, H.; Kim, D. I.; Kunkel, M.; Powis, G.; Zalkow, L. H. Bioorg. Med. Chem. 2001, 9, 1073-1083.
-
(2001)
Bioorg. Med. Chem
, vol.9
, pp. 1073-1083
-
-
Xie, W.1
Peng, H.2
Kim, D.I.3
Kunkel, M.4
Powis, G.5
Zalkow, L.H.6
-
52
-
-
33746494993
-
-
Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011-1013.
-
(1978)
J. Org. Chem
, vol.43
, pp. 1011-1013
-
-
Ito, Y.1
Hirao, T.2
Saegusa, T.3
-
53
-
-
0033543478
-
-
Egner, U.; Fritzemeier, K.-H.; Halfbrodt, W.; Heinrich, N.; Kuhnke, J.; Muller-Fahrnow, A.; Neef, G.; Schollkopf, K.; Schwede, W. Tetrahedron 1999, 55, 11267-11274.
-
(1999)
Tetrahedron
, vol.55
, pp. 11267-11274
-
-
Egner, U.1
Fritzemeier, K.-H.2
Halfbrodt, W.3
Heinrich, N.4
Kuhnke, J.5
Muller-Fahrnow, A.6
Neef, G.7
Schollkopf, K.8
Schwede, W.9
-
54
-
-
34250793991
-
-
When THF was used as the solvent, we isolated a side product in 10% yield in which the triflate functionality was reduced and the indoline ring was oxidized to the corresponding indole. This oxidation most likely occurred via air oxidation during the purification stage. However, we later found that, when THF was replaced with dioxane as the solvent, only the desired heptacyclic indole (+)-51 was obtained.
-
When THF was used as the solvent, we isolated a side product in 10% yield in which the triflate functionality was reduced and the indoline ring was oxidized to the corresponding indole. This oxidation most likely occurred via air oxidation during the purification stage. However, we later found that, when THF was replaced with dioxane as the solvent, only the desired heptacyclic indole (+)-51 was obtained.
-
-
-
|