-
1
-
-
0025160288
-
Discodermolide: A new bioactive polyhydroxylated lactone from the marine sponge Discodermia dissoluta
-
Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Schulte, G. K. Discodermolide: a new bioactive polyhydroxylated lactone from the marine sponge Discodermia dissoluta. J. Org. Chem. 1990, 55, 4912-4915; correction: Ibid. 1991, 56, 1346.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 4912-4915
-
-
Gunasekera, S.P.1
Gunasekera, M.2
Longley, R.E.3
Schulte, G.K.4
-
2
-
-
85022401932
-
-
correction
-
Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Schulte, G. K. Discodermolide: a new bioactive polyhydroxylated lactone from the marine sponge Discodermia dissoluta. J. Org. Chem. 1990, 55, 4912-4915; correction: Ibid. 1991, 56, 1346.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 1346
-
-
-
3
-
-
0030039669
-
Discodermolide, a cytotoxic marine agent that stabilizes microtubules more potently than taxol
-
Ter Haar, E.; Kowalski, R. J.; Hamel, E.; Lin, C. M.; Longley, R. E.; Gunasekera, S. P.; Rosenkranz, H. S.; Day, B. W. Discodermolide, a cytotoxic marine agent that stabilizes microtubules more potently than taxol. Biochemistry 1996, 35, 243-250.
-
(1996)
Biochemistry
, vol.35
, pp. 243-250
-
-
Ter Haar, E.1
Kowalski, R.J.2
Hamel, E.3
Lin, C.M.4
Longley, R.E.5
Gunasekera, S.P.6
Rosenkranz, H.S.7
Day, B.W.8
-
4
-
-
0034826406
-
The relationship between Taxol and (+)-discodermolide: Synthetic analogues and modeling studies
-
Martello, L. A.; LaMarche, M. J.; He, L.; Beauchamp, T. J.; Smith, A. B., III.; Horwitz, S. B. The relationship between Taxol and (+)-discodermolide: synthetic analogues and modeling studies. Chem. Biol. 2001, 8, 843-855.
-
(2001)
Chem. Biol.
, vol.8
, pp. 843-855
-
-
Martello, L.A.1
LaMarche, M.J.2
He, L.3
Beauchamp, T.J.4
Smith A.B. III5
Horwitz, S.B.6
-
5
-
-
0029860912
-
Syntheses of discodermolides useful for investigating microtubule binding and stabilization
-
Hung, D. T.; Nerenberg, J. B.; Schreiber, S. L. Syntheses of discodermolides useful for investigating microtubule binding and stabilization. J. Am. Chem. Soc. 1996, 118, 11054-11080.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 11054-11080
-
-
Hung, D.T.1
Nerenberg, J.B.2
Schreiber, S.L.3
-
6
-
-
18844469806
-
Taxol and discodermolide represent a synergistic drug combination in human carcinoma cell lines
-
Martello, L. A.; McDaid, H. M.; Regl, D.; Yang, C. P.; Meng, D.; Pettus, T. R. R.; Kaufman, M. D.; Arimoto, H.; Danishefsky, S. J.; Smith, A. B., III.; Horwitz, S. B. Taxol and discodermolide represent a synergistic drug combination in human carcinoma cell lines. Clin. Cancer Res. 2000, 6, 1978-1987.
-
(2000)
Clin. Cancer Res.
, vol.6
, pp. 1978-1987
-
-
Martello, L.A.1
McDaid, H.M.2
Regl, D.3
Yang, C.P.4
Meng, D.5
Pettus, T.R.R.6
Kaufman, M.D.7
Arimoto, H.8
Danishefsky, S.J.9
Smith A.B. III10
Horwitz, S.B.11
-
7
-
-
0035802349
-
A practical synthesis of (+)-discodermolide and analogues: Fragment union by complex aldol reactions
-
Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P.; Sereinig, N. A practical synthesis of (+)-discodermolide and analogues: fragment union by complex aldol reactions. J. Am. Chem. Soc. 2001, 123, 9535-9544.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 9535-9544
-
-
Paterson, I.1
Florence, G.J.2
Gerlach, K.3
Scott, J.P.4
Sereinig, N.5
-
8
-
-
0034644383
-
Evolution of a gram-scale synthesis of (+)-discodermolide
-
Smith, A. B., III.; Beauchamp, T. J.; LaMarche, M. J.; Kaufman, M. D.; Qui, Y.; Arimoto, H.; Jones, D. R.; Kobayashi, K. Evolution of a gram-scale synthesis of (+)-discodermolide. J. Am. Chem. Soc. 2000, 122, 8654-8664.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 8654-8664
-
-
Smith A.B. III1
Beauchamp, T.J.2
LaMarche, M.J.3
Kaufman, M.D.4
Qui, Y.5
Arimoto, H.6
Jones, D.R.7
Kobayashi, K.8
-
9
-
-
0030772544
-
Total synthesis of (-)-discodermolide: An application of a chelation-controlled alkylation reaction
-
Harried, S. S.; Yang, G.; Strawn, M. A.; Myles, D. C. Total synthesis of (-)-discodermolide: an application of a chelation-controlled alkylation reaction. J. Org. Chem. 1997, 62, 6098-6099.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 6098-6099
-
-
Harried, S.S.1
Yang, G.2
Strawn, M.A.3
Myles, D.C.4
-
10
-
-
0032582745
-
Total synthesis of (+)-discodermolide
-
Marshall, J. A.; Johns, B. A. Total synthesis of (+)-discodermolide. J. Org. Chem. 1998, 63, 7885-7892.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 7885-7892
-
-
Marshall, J.A.1
Johns, B.A.2
-
11
-
-
0037150581
-
Convenient syntheses of (2S, 3S, 4R)-3-tert-butyldimethylsilanyloxy)-2,4-dimethyl-5-oxopentanoic acid methoxymethylamide from methacrolein. Preparation of C1-C17 and C17-C24 fragments of (+)-discodermolide
-
and references therein
-
Day, B. W.; Kangani, C. O.; Avor, K. S. Convenient syntheses of (2S, 3S, 4R)-3-tert-butyldimethylsilanyloxy)-2,4-dimethyl-5-oxopentanoic acid methoxymethylamide from methacrolein. Preparation of C1-C17 and C17-C24 fragments of (+)-discodermolide. Tetrahedron: Asymmetry 2002, 13, 1161-1165 and references therein.
-
(2002)
Tetrahedron: Asymmetry
, vol.13
, pp. 1161-1165
-
-
Day, B.W.1
Kangani, C.O.2
Avor, K.S.3
-
12
-
-
0035089418
-
Acetylated analogues of the microtubule-stabilizing agent discodermolide: Preparation and biological activities
-
Gunasekera, S. P.; Longley, R. E.; Isbrucker, R. A. Acetylated analogues of the microtubule-stabilizing agent discodermolide: preparation and biological activities. J. Nat. Prod. 2001, 64, 171-174.
-
(2001)
J. Nat. Prod.
, vol.64
, pp. 171-174
-
-
Gunasekera, S.P.1
Longley, R.E.2
Isbrucker, R.A.3
-
13
-
-
0034913460
-
Structure-activity relationship studies of discodermolide and its semisynthetic acetylated analogues on microtubule function and cytotoxicity
-
Isbrucker, R. A.; Gunasekera, S. P.; Longley, R. E. Structure-activity relationship studies of discodermolide and its semisynthetic acetylated analogues on microtubule function and cytotoxicity. Cancer Chemother. Pharmacol. 2001, 48, 29-36.
-
(2001)
Cancer Chemother. Pharmacol.
, vol.48
, pp. 29-36
-
-
Isbrucker, R.A.1
Gunasekera, S.P.2
Longley, R.E.3
-
14
-
-
0034674252
-
Conformation design of open-chain compounds
-
and references therein
-
Hoffmann, R. W. Conformation design of open-chain compounds. Angew. Chem., Int. Ed. 2000, 39, 2054-2070 and references therein.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 2054-2070
-
-
Hoffmann, R.W.1
-
15
-
-
0037832515
-
Synthesis and high content cell-based profiling of simplified analogues of the potent microtubule stabilizer (+)-discodermolide
-
(a) Minguez, J. M.; Balachandran, R.; Giuliano, K. A.; Madiraju, C.; Curran, D. P.; Day, B. W. Synthesis and high content cell-based profiling of simplified analogues of the potent microtubule stabilizer (+)-discodermolide. Mol. Cancer Ther. 2002, 1, 1305-1313.
-
(2002)
Mol. Cancer Ther.
, vol.1
, pp. 1305-1313
-
-
Minguez, J.M.1
Balachandran, R.2
Giuliano, K.A.3
Madiraju, C.4
Curran, D.P.5
Day, B.W.6
-
16
-
-
0038354572
-
Synthesis and biological assessment of simplified analogues of the potent microtubule stabilizer (+)-discodermolide
-
in press
-
(b) Minguez, J. M.; Kim, S.-Y.; Balachandran, R.; Madiraju, C.; Day, B. W.; Curran, D. P. Synthesis and biological assessment of simplified analogues of the potent microtubule stabilizer (+)-discodermolide, Bioorg. Med. Chem., in press.
-
Bioorg. Med. Chem.
-
-
Minguez, J.M.1
Kim, S.-Y.2
Balachandran, R.3
Madiraju, C.4
Day, B.W.5
Curran, D.P.6
-
17
-
-
0035826325
-
Solution structure of (+)-discodermolide
-
Smith, A. B., III.; LaMarche, M. J.; Falcone-Hindley, M. Solution structure of (+)-discodermolide. Org. Lett. 2001, 3, 695-698.
-
(2001)
Org. Lett.
, vol.3
, pp. 695-698
-
-
Smith A.B. III1
LaMarche, M.J.2
Falcone-Hindley, M.3
-
18
-
-
0034829880
-
The conformation of discodermolide in DMSO
-
Monteagudo, E.; Cicero, D. O.; Cornett, B.; Myles, D. C.; Synder, J. P. The conformation of discodermolide in DMSO. J. Am. Chem. Soc. 2001, 123, 6929-6930.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 6929-6930
-
-
Monteagudo, E.1
Cicero, D.O.2
Cornett, B.3
Myles, D.C.4
Synder, J.P.5
-
19
-
-
0037182696
-
Simultaneous preparation of four truncated analogues of discodermolide by fluorous mixture synthesis
-
Curran, D. P.; Furukawa, T. Simultaneous preparation of four truncated analogues of discodermolide by fluorous mixture synthesis. Org. Lett. 2002, 4, 2233-2235.
-
(2002)
Org. Lett.
, vol.4
, pp. 2233-2235
-
-
Curran, D.P.1
Furukawa, T.2
-
20
-
-
0037598989
-
-
note
-
As an initial trial, we used the lactone-aldehyde protected with MOM for the Wittig reaction. Due to the low yield as well as the elimination of the C3 hydroxyl group, the methyl acetal aldehyde was used instead.
-
-
-
-
21
-
-
0031038054
-
Enantioselective synthesis of the elaiophylin aglycon
-
Evans, D. A.; Fitch, D. M. Enantioselective synthesis of the elaiophylin aglycon. J. Org. Chem. 1997, 62, 454-455.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 454-455
-
-
Evans, D.A.1
Fitch, D.M.2
-
22
-
-
0028929730
-
Synthetic studies toward mono-THF annonaceous acetogenines: A diastereoselective and convergent approach to corossolone and (10RS)-corossoline
-
Yao, Z.; Wu, Y. Synthetic studies toward mono-THF annonaceous acetogenines: a diastereoselective and convergent approach to corossolone and (10RS)-corossoline. J. Org. Chem. 1995, 60, 1170-1176.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 1170-1176
-
-
Yao, Z.1
Wu, Y.2
-
23
-
-
0027380737
-
Studies on the alkylation of chiral enolates: Application toward the total synthesis of discodermolide
-
Clark, D. L.; Heathcock, C. H. Studies on the alkylation of chiral enolates: application toward the total synthesis of discodermolide. J. Org. Chem. 1993, 58 5878-5879.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 5878-5879
-
-
Clark, D.L.1
Heathcock, C.H.2
-
24
-
-
0037069732
-
Discodermolide/Dictyostatin hybrids: Synthesis and biological evaluation
-
Shin, Y.; Choy, N.; Turner, T. R.; Balachandran, R.; Madiraju, C.; Day, B. W.; Curran, D. P. Discodermolide/Dictyostatin hybrids: synthesis and biological evaluation. Org. Lett. 2002, 4, 4443-4446.
-
(2002)
Org. Lett.
, vol.4
, pp. 4443-4446
-
-
Shin, Y.1
Choy, N.2
Turner, T.R.3
Balachandran, R.4
Madiraju, C.5
Day, B.W.6
Curran, D.P.7
-
25
-
-
0027771890
-
The asymmetric syntheses of the C-1 side chains of zaragozic acid A and zaragozic acid C
-
Robichaud, A. J.; Berger, G. D.; Evans D. A. The asymmetric syntheses of the C-1 side chains of zaragozic acid A and zaragozic acid C. Tetrahedron Lett. 1993, 34 8403-8406.
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 8403-8406
-
-
Robichaud, A.J.1
Berger, G.D.2
Evans, D.A.3
-
26
-
-
0038274259
-
-
note
-
Model studies had shown that isopropylmagnesium chloride could be added to aldehyde 49 to give the expected compound as a major product. The configuration of the hydroxy group in the major diastereomer was assigned by the Felkin-Ahn model. DDQ oxidation of the major product afforded cyclic acetal 59. NOESY studies of this cyclic acetal showed that the relative configuration of the PMB hydroxy group at C17 and a newly formed hydroxy group at C19 in parent molecule were syn to each other. Equation Presented
-
-
-
-
27
-
-
0037598990
-
-
note
-
Alternatively, the secondary alcohol of compound 38 could be protected with PMB under basic conditions from the Weinreb amide (not shown) in good yield without any evidence of epimerization. DIBAL reduction then afforded aldehyde 49 in good yield.
-
-
-
-
28
-
-
0000190244
-
Acyclic stereoselection-13; Aryl esters: Reagents for threoaldolization
-
Heathcock, C. H.; Pirrung, M. C.; Montgomery, S. H.; Lampe, J. Acyclic stereoselection-13; Aryl esters: reagents for threoaldolization. Tetrahedron 1981, 37, 4087-4095.
-
(1981)
Tetrahedron
, vol.37
, pp. 4087-4095
-
-
Heathcock, C.H.1
Pirrung, M.C.2
Montgomery, S.H.3
Lampe, J.4
-
29
-
-
33751385878
-
13C NMR correlations for determining the stereochemistry of 1,3-diol acetonides
-
13C NMR correlations for determining the stereochemistry of 1,3-diol acetonides. J. Org. Chem. 1993, 58, 3511-3515.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 3511-3515
-
-
Rychnovsky, S.D.1
Rogers, B.2
Yang, G.3
-
30
-
-
0000693499
-
Studies towards the total synthesis of the marine-derived immunosuppressant discodermolide: Stereo-selective synthesis of a C9-C24 subunit
-
Paterson, I.; Schlapbach, A. Studies towards the total synthesis of the marine-derived immunosuppressant discodermolide: stereo-selective synthesis of a C9-C24 subunit. Synlett 1995, 498-500.
-
(1995)
Synlett
, pp. 498-500
-
-
Paterson, I.1
Schlapbach, A.2
-
31
-
-
0002225909
-
Trimethylsilylation of carbenoids generated in situ from allyl and benzyl halides
-
Andringa, H.; Heus-klos, Y. A.; Brandsma, L. Trimethylsilylation of carbenoids generated in situ from allyl and benzyl halides. J. Organomet. Chem. 1987, 336, C41-C43.
-
(1987)
J. Organomet. Chem.
, vol.336
-
-
Andringa, H.1
Heus-Klos, Y.A.2
Brandsma, L.3
-
32
-
-
0022966219
-
Carbamates: A method of synthesis and some synthetic applications
-
Koçovsky, P. Carbamates: a method of synthesis and some synthetic applications. Tetrahedron Lett. 1986, 27 5521-5524.
-
(1986)
Tetrahedron Lett.
, vol.27
, pp. 5521-5524
-
-
Koçovsky, P.1
-
33
-
-
0037936978
-
Asymmetric total syntheses of (+)- and (-)-pulo'upone
-
Sugahara, T.; Iwata, T.; Yamaoka, M.; Takano, S. Asymmetric total syntheses of (+)- and (-)-pulo'upone. Tetrahedron Lett. 1989, 30, 1821-1824.
-
(1989)
Tetrahedron Lett.
, vol.30
, pp. 1821-1824
-
-
Sugahara, T.1
Iwata, T.2
Yamaoka, M.3
Takano, S.4
-
34
-
-
0021163546
-
Separation of active tubulin and microtubule-associated proteins by ultracentrifugation and isolation of a component causing the formation of microtubule bundles
-
Hamel, E.; Lin, C. M. Separation of active tubulin and microtubule-associated proteins by ultracentrifugation and isolation of a component causing the formation of microtubule bundles. Biochemistry 1984, 23, 4173-4184.
-
(1984)
Biochemistry
, vol.23
, pp. 4173-4184
-
-
Hamel, E.1
Lin, C.M.2
-
35
-
-
0033609037
-
The coral-derived natural products eleutherobin and sarcodictyins A and B: Effects on the assembly of purified tubulin with and without microtubule-associated proteins and binding at the polymer taxoid site
-
Hamel, E.; Sackett, D. L.; Vourloumis, D.; Nicolaou, K. C. The coral-derived natural products eleutherobin and sarcodictyins A and B: effects on the assembly of purified tubulin with and without microtubule-associated proteins and binding at the polymer taxoid site. Biochemistry 1999, 38, 5490-5498.
-
(1999)
Biochemistry
, vol.38
, pp. 5490-5498
-
-
Hamel, E.1
Sackett, D.L.2
Vourloumis, D.3
Nicolaou, K.C.4
-
36
-
-
0034605473
-
Synthesis and biological evaluation of a focused mixture library of analogues of the antimitotic marine natural product curacin A
-
Wipf, P.; Reeves, J. T.; Balachandran, R.; Giuliano, K. A.; Hamel, E.; Day, B. W. Synthesis and biological evaluation of a focused mixture library of analogues of the antimitotic marine natural product curacin A. J. Am. Chem. Soc. 2000, 122, 9391-9395.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 9391-9395
-
-
Wipf, P.1
Reeves, J.T.2
Balachandran, R.3
Giuliano, K.A.4
Hamel, E.5
Day, B.W.6
-
37
-
-
0030761586
-
The microtubule-stabilizing agent discodermolide competitively inhibits the binding of paclitaxel (Taxol) to tubulin polymers, enhances tubulin nucleation reactions more potently than paclitaxel, and inhibits the growth of paclitaxel-resistant cells
-
Kowalski, R. J.; Giannakakou, P.; Gunasekera, S. P.; Longley, R. E.; Day, B. W.; Hamel, E. The microtubule-stabilizing agent discodermolide competitively inhibits the binding of paclitaxel (Taxol) to tubulin polymers, enhances tubulin nucleation reactions more potently than paclitaxel, and inhibits the growth of paclitaxel-resistant cells. Mol. Pharmacol. 1997, 52, 613-622.
-
(1997)
Mol. Pharmacol.
, vol.52
, pp. 613-622
-
-
Kowalski, R.J.1
Giannakakou, P.2
Gunasekera, S.P.3
Longley, R.E.4
Day, B.W.5
Hamel, E.6
|