-
1
-
-
0026321672
-
-
Manfredi, K. P.; Blunt, J. W.; Cardellina, J. H.; McMahon, J. B.; Pannell, L. L.; Cragg, G. M.; Boyd, M. R. J. Med. Chem. 1991, 34, 3402.
-
(1991)
J. Med. Chem.
, vol.34
, pp. 3402
-
-
Manfredi, K.P.1
Blunt, J.W.2
Cardellina, J.H.3
McMahon, J.B.4
Pannell, L.L.5
Cragg, G.M.6
Boyd, M.R.7
-
2
-
-
0028246682
-
-
Boyd, M. R.; Hallock, Y. F.; Cardellina, J. H.; Manfredi, K. P.; Blunt, J. W.; McMahon, J. B.; Buckheit, R. W.; Bringmann, G.; Schäffer, M.; Cragg, G. M.; Thomas, D. W.; Jato, J. G. J. Med. Chem. 1994, 37, 1740.
-
(1994)
J. Med. Chem.
, vol.37
, pp. 1740
-
-
Boyd, M.R.1
Hallock, Y.F.2
Cardellina, J.H.3
Manfredi, K.P.4
Blunt, J.W.5
McMahon, J.B.6
Buckheit, R.W.7
Bringmann, G.8
Schäffer, M.9
Cragg, G.M.10
Thomas, D.W.11
Jato, J.G.12
-
4
-
-
0028878344
-
-
McMahon, J. B.; Currens, M. J.; Gulakowski, R. J.; Buckheit, R. W.; Lackman-Smith, C.; Hallock, Y. F.; Boyd, M. R. Antimicrob. Agents Chemother. 1995, 39, 484.
-
(1995)
Antimicrob. Agents Chemother.
, vol.39
, pp. 484
-
-
McMahon, J.B.1
Currens, M.J.2
Gulakowski, R.J.3
Buckheit, R.W.4
Lackman-Smith, C.5
Hallock, Y.F.6
Boyd, M.R.7
-
7
-
-
0000175810
-
The naphthyl isoquinoline alkaloids
-
Brossi, A., Ed.; Academic Press: New York, Chapter 3
-
(a) Bringmann, G. The Naphthyl Isoquinoline Alkaloids. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 29, Chapter 3.
-
(1986)
The Alkaloids
, vol.29
-
-
Bringmann, G.1
-
8
-
-
0001615014
-
The naphthylisoquinoline alkaloids
-
Cordell, G., Ed.; Academic Press: New York, Chapter 4
-
(b) Bringmann, G.; Pokorny, F. The Naphthylisoquinoline Alkaloids. In The Alkaloids; Cordell, G., Ed.; Academic Press: New York, 1995; Vol. 46, Chapter 4.
-
(1995)
The Alkaloids
, vol.46
-
-
Bringmann, G.1
Pokorny, F.2
-
9
-
-
33748983968
-
-
(a) Bringmann, G.; Zagst, R.; Schäffer, M.; Hallock, Y. F.; Cardellina, J. H., II; Boyd, M. R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1190.
-
(1993)
Angew. Chem., Int. Ed. Engl.
, vol.32
, pp. 1190
-
-
Bringmann, G.1
Zagst, R.2
Schäffer, M.3
Hallock, Y.F.4
Cardellina J.H. II5
Boyd, M.R.6
-
10
-
-
0030484489
-
-
(b) Bringmann, G.; God, R.; Schäffer, M. Phytochemistry 1996, 43, 1393.
-
(1996)
Phytochemistry
, vol.43
, pp. 1393
-
-
Bringmann, G.1
God, R.2
Schäffer, M.3
-
11
-
-
0027994893
-
-
Hallock, Y. F.; Manfredi, K. P.; Blunt, J. W. C.; Cardellina, J. H., II; Schäffer, M.; Gulden, K. P.; Bringmann, G.; Lee, A. Y.; Clardy, J.; François, G.; Boyd, M. R. J. Org. Chem. 1994, 59, 6349.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 6349
-
-
Hallock, Y.F.1
Manfredi, K.P.2
Blunt, J.W.C.3
Cardellina J.H. II4
Schäffer, M.5
Gulden, K.P.6
Bringmann, G.7
Lee, A.Y.8
Clardy, J.9
François, G.10
Boyd, M.R.11
-
12
-
-
0000211423
-
-
Bringmann, G.; Zagst, R.; Reusher, H.; Aké Assi, L. Phytochemistry 1992, 31, 4011.
-
(1992)
Phytochemistry
, vol.31
, pp. 4011
-
-
Bringmann, G.1
Zagst, R.2
Reusher, H.3
Aké Assi, L.4
-
13
-
-
0344170099
-
-
note
-
Compound supply was problematic, since the only known natural source was the rare A. korupensis liana, which is found only in a limited region of the Cameroonian rainforest.
-
-
-
-
14
-
-
0028130029
-
-
(a) Bringmann, G.; Harmsen, S.; Holenz, J.; Geuder, T.; Götz, R.; Keller, P. A.; Walter, R.; Hallock, Y. F.; Cardellina, J. H., II; Boyd, M. R. Tetrahedron 1994, 50, 9643.
-
(1994)
Tetrahedron
, vol.50
, pp. 9643
-
-
Bringmann, G.1
Harmsen, S.2
Holenz, J.3
Geuder, T.4
Götz, R.5
Keller, P.A.6
Walter, R.7
Hallock, Y.F.8
Cardellina J.H. II9
Boyd, M.R.10
-
15
-
-
0027970221
-
-
(b) Kelly, T. R.; Garcia, A.; Lang, F.; Walsh, J. J.; Bhaskar, K. V.; Boyd, M. R.; Götz, R.; Keller, P.; Walter, R.; Bringmann, G. Tetrahedron Lett. 1994, 35, 7621.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 7621
-
-
Kelly, T.R.1
Garcia, A.2
Lang, F.3
Walsh, J.J.4
Bhaskar, K.V.5
Boyd, M.R.6
Götz, R.7
Keller, P.8
Walter, R.9
Bringmann, G.10
-
16
-
-
0028020526
-
-
Hoye, T. R.; Chen, M.; Mi, L.; Priest, O. P. Tetrahedron Lett. 1994, 35, 8747.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 8747
-
-
Hoye, T.R.1
Chen, M.2
Mi, L.3
Priest, O.P.4
-
17
-
-
0029874643
-
-
Hobbs, P. W.; Upender, V.; Liu, J.; Pollart, D. J.; Thomas, D. W.; Dawson, M. I. J. Chem. Soc., Chem. Commun. 1996, 923.
-
(1996)
J. Chem. Soc., Chem. Commun.
, pp. 923
-
-
Hobbs, P.W.1
Upender, V.2
Liu, J.3
Pollart, D.J.4
Thomas, D.W.5
Dawson, M.I.6
-
18
-
-
33748974785
-
-
(e) Bringmann, G.; Götz, R.; Harmsen, S.; Holenz, J.; Walter, R. Liebigs Ann. 1996, 12, 2045.
-
(1996)
Liebigs Ann.
, vol.12
, pp. 2045
-
-
Bringmann, G.1
Götz, R.2
Harmsen, S.3
Holenz, J.4
Walter, R.5
-
20
-
-
7144259775
-
-
(g) Bringmann, G.; Götz, R.; Keller, P. A.; Walter, R.; Boyd, M. R.; Lang, F.; Garcia, A.; Walsh, J. J.; Tellitu I.; Bhaskar, K. V.; Kelly, T. R. J. Org. Chem. 1998, 63, 1090-1097.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 1090-1097
-
-
Bringmann, G.1
Götz, R.2
Keller, P.A.3
Walter, R.4
Boyd, M.R.5
Lang, F.6
Garcia, A.7
Walsh, J.J.8
Tellitu, I.9
Bhaskar, K.V.10
Kelly, T.R.11
-
21
-
-
0029798494
-
-
(h) Upender, V.; Pollart, D. J.; Liu, J.; Hobbs, P. D.; Olsen, C.; Chao, W.; Bowden, B.; Crase, J. L.; Thomas, D. W.; Pandey, A.; Lawson, J. A.; Dawson, M. I. J. Heterocycl. Chem. 1996, 33, 1371.
-
(1996)
J. Heterocycl. Chem.
, vol.33
, pp. 1371
-
-
Upender, V.1
Pollart, D.J.2
Liu, J.3
Hobbs, P.D.4
Olsen, C.5
Chao, W.6
Bowden, B.7
Crase, J.L.8
Thomas, D.W.9
Pandey, A.10
Lawson, J.A.11
Dawson, M.I.12
-
22
-
-
0030668534
-
-
Zhang, H. P.; Zembower, D. E.; Chen, Z. D. Bioorg. Med. Chem. Lett. 1997, 7, 2687.
-
(1997)
Bioorg. Med. Chem. Lett.
, vol.7
, pp. 2687
-
-
Zhang, H.P.1
Zembower, D.E.2
Chen, Z.D.3
-
23
-
-
0033524775
-
-
(j) Bringmann, G., Wenzel, M.; Kelly, T. R.; Boyd, M. R.; Gulakowski, R. J.; Kaminsky, R. Tetrahedron 1999, 55, 1731-1740.
-
(1999)
Tetrahedron
, vol.55
, pp. 1731-1740
-
-
Bringmann, G.1
Wenzel, M.2
Kelly, T.R.3
Boyd, M.R.4
Gulakowski, R.J.5
Kaminsky, R.6
-
24
-
-
0033537934
-
-
(k) de Koning, C. B.; Michael, J. P.; van Otterlo, W. Tetrahedron Lett 1999, 40, 3037.
-
(1999)
Tetrahedron Lett
, vol.40
, pp. 3037
-
-
De Koning, C.B.1
Michael, J.P.2
Van Otterlo, W.3
-
25
-
-
0344601740
-
-
note
-
12b
-
-
-
-
26
-
-
0001537132
-
-
(a) Bringmann, G.; Götz, R.; Ketter, P. A.; Walter, R.; Henschel, P.; Schäffer, M.; Stablein, M.; Kelly, T. R.; Boyd, M. R. Heterocycles 1994, 39, 503.
-
(1994)
Heterocycles
, vol.39
, pp. 503
-
-
Bringmann, G.1
Götz, R.2
Ketter, P.A.3
Walter, R.4
Henschel, P.5
Schäffer, M.6
Stablein, M.7
Kelly, T.R.8
Boyd, M.R.9
-
27
-
-
0345628806
-
-
(b) Rao, A. V. R.; Gurjar, M. K.; Ramana, D. V.; Chheda, A. K. Heterocycles 1996, 43, 1.
-
(1996)
Heterocycles
, vol.43
, pp. 1
-
-
Rao, A.V.R.1
Gurjar, M.K.2
Ramana, D.V.3
Chheda, A.K.4
-
31
-
-
0022966050
-
-
(a) Bringmann, G.; Jansen, J. R.; Rink, H.-P. Angew. Chem., Int. Ed. Engl. 1986, 25, 913-915.
-
(1986)
Angew. Chem., Int. Ed. Engl.
, vol.25
, pp. 913-915
-
-
Bringmann, G.1
Jansen, J.R.2
Rink, H.-P.3
-
32
-
-
84988122964
-
-
(b) Bringmann, G.; Weirich, R.; Reuscher, H.; Jansen, J. R.; Kinzinger, L.; Ortmann, T. Liebigs Ann. Chem. 1993, 877.
-
(1993)
Liebigs Ann. Chem.
, pp. 877
-
-
Bringmann, G.1
Weirich, R.2
Reuscher, H.3
Jansen, J.R.4
Kinzinger, L.5
Ortmann, T.6
-
33
-
-
0345463733
-
-
note
-
For example, cycloaddition of benzyne i (derived from iodotriflate ii by treatment with n-BuLi) with 4-(2-furyl)anisole (iii) gave the undesired regioisomer iv as the only product. We also examined the cycloaddition of benzyne i with THIQ substituted furan v. However, no cycloaddition products were observed, probably because of the hindered nature of v. equation presented
-
-
-
-
34
-
-
0022442643
-
-
Watanabe, M.; Hisamatsu, S.; Hotokezaka, H.; Furukawa, S. Chem. Pharm. Bull. 1986, 34, 2810.
-
(1986)
Chem. Pharm. Bull.
, vol.34
, pp. 2810
-
-
Watanabe, M.1
Hisamatsu, S.2
Hotokezaka, H.3
Furukawa, S.4
-
35
-
-
0345032656
-
-
note
-
Modifications included changing the number of equivalents of dialkylamide anion, the order and rate of addition, the number of equivalents of dibromide precursor, the solvent, the structure of the dialkylamide base, and the temperature of benzyne generation and reaction. n-Butyllithium was used for the preliminary deprotonation of β,β-dimethyl-N,N-diethylacrylamide (in an attempt to reduce the amount of isopropylcyclohexylamine and the amount of amine-trapped product 19). However, none of these modifications resulted in significant changes in the yield or ratio of products.
-
-
-
-
38
-
-
0027194218
-
-
Li, G.; Patel, D.; Hruby, V. J. Tetrahedron Lett. 1993, 34, 5393.
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 5393
-
-
Li, G.1
Patel, D.2
Hruby, V.J.3
-
39
-
-
0029022489
-
-
Cf. the C(1)-epimerization proposed to explain the coexistence of gentryamines A (vi) and B (vii) in A. korupensis: Hallock, Y. F.; Cardellina, J. H.; Korneck, T.; Gulden, K. P.; Bringmann, G.; Boyd, M. R. Tetrahedron Lett. 1995, 36, 4753. equation presented
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 4753
-
-
Hallock, Y.F.1
Cardellina, J.H.2
Korneck, T.3
Gulden, K.P.4
Bringmann, G.5
Boyd, M.R.6
-
40
-
-
0344601736
-
-
note
-
12f The resulting 6,8-dihydrory-N-benzylated THIQ (ix.) was converted efficiently to ent-22. equation presented
-
-
-
-
41
-
-
0003412112
-
-
Hoye, T. R.; Renner, M. K.; Vos-Dinardo, T. J. J. Org. Chem. 1997, 26, 4168.
-
(1997)
J. Org. Chem.
, vol.26
, pp. 4168
-
-
Hoye, T.R.1
Renner, M.K.2
Vos-Dinardo, T.J.3
-
42
-
-
0345463726
-
-
note
-
While the diastereoselectivity favoring the indicated C(1)-epimer of 38 was only 88% de when the reaction was performed at rt, it rose to 96% de for samples arising from reactions begun at -78 °C and then slowly warmed to rt.
-
-
-
-
43
-
-
7044232208
-
-
Reny, J.; Wang, C. Y.; Bushweller, C. H.; Anderson, W. G. Tetrahedron Lett. 1975, 503.
-
(1975)
Tetrahedron Lett.
, pp. 503
-
-
Reny, J.1
Wang, C.Y.2
Bushweller, C.H.3
Anderson, W.G.4
-
47
-
-
0015690693
-
-
(c) Rylander, P. N.; Hasbrouck, L.; Karpenko, I. Annals of the New York Academy of Sciences 1973, 214, 100.
-
(1973)
Annals of the New York Academy of Sciences
, vol.214
, pp. 100
-
-
Rylander, P.N.1
Hasbrouck, L.2
Karpenko, I.3
-
48
-
-
0344601734
-
-
note
-
3, ether, RT) and displacement with potassium cyanide (aqueous ethanol, reflux).
-
-
-
-
49
-
-
33748605775
-
-
For a review describing the use of chiral aziridines in synthesis, see: Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
-
(1994)
Angew. Chem., Int. Ed. Engl.
, vol.33
, pp. 599
-
-
Tanner, D.1
-
50
-
-
0344170075
-
-
note
-
We appreciate Professor Bruce H. Lipshutz sharing his group's expertise in surmounting this problem.
-
-
-
-
51
-
-
0000902959
-
-
Daub, G. W.; Heerding, D. A.; Overman, L. E. Tetrahedron 1988, 44, 3919.
-
(1988)
Tetrahedron
, vol.44
, pp. 3919
-
-
Daub, G.W.1
Heerding, D.A.2
Overman, L.E.3
-
52
-
-
0346471289
-
-
Lipshutz, B. H.; Siegmann, K.; Garcia, E. Kayser, F. J. Am. Chem. Soc. 1993, 115, 9276.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 9276
-
-
Lipshutz, B.H.1
Siegmann, K.2
Garcia, E.3
Kayser, F.4
-
53
-
-
0344601730
-
-
note
-
The acetate analogue of 49 (xiii) was once prepared by coupling the naphthyl triflate xi with the THIQ boronic acid xii. The triflate was derived from the naphthalene-1,4-diol i, which in turn could be prepared by the indicated Diels-Alder reactions. This strategy was inferior to the THIQ-halide/naphthalene-metal routes we adopted (Chart 1) because the synthesis of x was not efficient and the generation of boronic acid xii made the sequence less convergent with respect to the more complex THIQ unit. equation presented
-
-
-
-
55
-
-
0028352466
-
-
(a) Bringmann, G.; Gulden, K. P.; Hallock, Y. F.; Manfredi, K. P.; Cardellina, J. H.; Boyd, M. R.; Kramer, B.; Fleischhauer, J. Tetrahedron 1994, 50, 7807.
-
(1994)
Tetrahedron
, vol.50
, pp. 7807
-
-
Bringmann, G.1
Gulden, K.P.2
Hallock, Y.F.3
Manfredi, K.P.4
Cardellina, J.H.5
Boyd, M.R.6
Kramer, B.7
Fleischhauer, J.8
-
56
-
-
0031584896
-
-
(b) Bringmann, G.; Stahl, M.; Gulden, K. P. Tetrahedron 1997, 53, 2817.
-
(1997)
Tetrahedron
, vol.53
, pp. 2817
-
-
Bringmann, G.1
Stahl, M.2
Gulden, K.P.3
-
58
-
-
0345032639
-
-
note
-
The 4-aryl-substituted 1-naphthol (Ar = 2,4-dimethoxy-6-methylphenyl) xiv was readily coupled by silver oxide to the indigo-blue cross-ring quinone xv and then reduced to the binaphthol derivative xvi. equation presented
-
-
-
-
59
-
-
0024578841
-
-
Assays were performed under the Developmental Therapeutics Program at the National Cancer Institute. Protection of CEM-SS cells toward infection by HIV-1 was monitored by quantifying the number of viable cells using XTT/formazin colorimetric detection. Weislow, O. W.; Kiser, R.; Fine, D.; Bader, J.; Shoemaker, R. H.; Boyd, M. R. J. Natl. Cancer Inst. 1989, 81, 577.
-
(1989)
J. Natl. Cancer Inst.
, vol.81
, pp. 577
-
-
Weislow, O.W.1
Kiser, R.2
Fine, D.3
Bader, J.4
Shoemaker, R.H.5
Boyd, M.R.6
|