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1
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0030824140
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(a) Isolation: Clark, W. D.; Corbett, T.; Valeriote, F.; Crews, P. J. Am. Chem. Soc. 1997, 119, 9285-9286.
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Clark, W.D.1
Corbett, T.2
Valeriote, F.3
Crews, P.4
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3
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0024410310
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(a) Swinholide A was identified by comparison to data in Kobayashi, M.; Tanaka, J.; Katori, T.; Matsuura, M.; Kitagawa, I. Tetrahedron Lett. 1989, 30, 2963-2966.
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Tetrahedron Lett.
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Kobayashi, M.1
Tanaka, J.2
Katori, T.3
Matsuura, M.4
Kitagawa, I.5
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4
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49549165124
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(b) Variabilin was identified by comparison to data in Faulkner, D. J. Tetrahedron Lett. 1973, 39, 3821-3822.
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(1973)
Tetrahedron Lett.
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Faulkner, D.J.1
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5
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0008286250
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(c) Polybrominated phenol ethers were identified by comparison to data in Bowden, B. F.; Towerzey, L.; Junk, P. C. Aust. J. Chem. 2000, 53, 299-301.
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Aust. J. Chem.
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Bowden, B.F.1
Towerzey, L.2
Junk, P.C.3
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7
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3042845090
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note
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3, q).
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-
-
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8
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85004388152
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Methylation of 1 was performed as described in Hashimoto, N.; Aoyama, T.; Shioiri, T. Chem. Pharm. Bull. 1981, 29, 1475-1478. Although we originally favored C1 as a possible substructure, we are grateful to an anonymous reviewer who noted the potential of phenols to undergo O-methylation (Toyohiko, A.; Terasawa, S.; Sudo, K.; Shioiri, T. Chem. Pharm. Bull. 1984, 32, 3759-3760.).
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(1981)
Chem. Pharm. Bull.
, vol.29
, pp. 1475-1478
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Hashimoto, N.1
Aoyama, T.2
Shioiri, T.3
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9
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85010090220
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Methylation of 1 was performed as described in Hashimoto, N.; Aoyama, T.; Shioiri, T. Chem. Pharm. Bull. 1981, 29, 1475-1478. Although we originally favored C1 as a possible substructure, we are grateful to an anonymous reviewer who noted the potential of phenols to undergo O-methylation (Toyohiko, A.; Terasawa, S.; Sudo, K.; Shioiri, T. Chem. Pharm. Bull. 1984, 32, 3759-3760.).
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(1984)
Chem. Pharm. Bull.
, vol.32
, pp. 3759-3760
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Toyohiko, A.1
Terasawa, S.2
Sudo, K.3
Shioiri, T.4
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10
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1242296319
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The name has been retained because of its prior incorporation in the research at collaborating institutions
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Shortly after the completion of this work we learned that iciniastatin A, possessing properties identical to those of psymberin (1) had been disclosed: Pettit, G. R.; Xu, J.-P.; Chapuis, J.-C.; Pettit, R. K.; Tackett, L. P.; Doubek, D. L.; Hooper, J. N. A.; Schmidt, J. M. J. Med. Chem. 2004, 47, 1149-1152. The name has been retained because of its prior incorporation in the research at collaborating institutions.
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Pettit, G.R.1
Xu, J.-P.2
Chapuis, J.-C.3
Pettit, R.K.4
Tackett, L.P.5
Doubek, D.L.6
Hooper, J.N.A.7
Schmidt, J.M.8
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11
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0033525048
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Matsumori, N.; Kaneno, D.; Murata, M.; Nakamura, H.; Tachibana, K. J. Org. Chem. 1999, 64, 866-876.
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Matsumori, N.1
Kaneno, D.2
Murata, M.3
Nakamura, H.4
Tachibana, K.5
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12
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0025263934
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Perry, N. B.; Blunt, J. W.; Munro, M. H. G.; Thompson, A. M. J. Org. Chem. 1990, 55, 223-227.
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Perry, N.B.1
Blunt, J.W.2
Munro, M.H.G.3
Thompson, A.M.4
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13
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3042851579
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note
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A different 7R* (same as position C-8 in psymberin, 1) configuration was proposed for irciniastatin A (see ref 5).
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14
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0348137906
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(a) Krohn, K.; Bahramsari, R.; Florke, U.; Ludewig, K.; Kliche-Spory, C.; Michel, A.; Aust, H.-J.; Draeger, S.; Schulz, B.; Antus, S. Phytochemistry 1997, 45, 313-320,
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(1997)
Phytochemistry
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Krohn, K.1
Bahramsari, R.2
Florke, U.3
Ludewig, K.4
Kliche-Spory, C.5
Michel, A.6
Aust, H.-J.7
Draeger, S.8
Schulz, B.9
Antus, S.10
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16
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0034571687
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Mulzer, J., Bohlmann, R., Eds.; Ernst Schering Research Foundation Workshop 32; Springer: New York, (b) See also Table S1
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(a) Narquizian, R.; Kocienski, P. J. In The Role of Natural Products in Drug Discovery; Mulzer, J., Bohlmann, R., Eds.; Ernst Schering Research Foundation Workshop 32; Springer: New York, 2000; pp 25-56. (b) See also Table S1.
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The Role of Natural Products in Drug Discovery
, pp. 25-56
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Narquizian, R.1
Kocienski, P.J.2
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17
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49949120719
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(a) Furusaki, A.; Watanabé, T.; Matsumoto, T.; Yanagiya, M. Tetrahedron Lett. 1968, 60, 6301-6304.
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Tetrahedron Lett.
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Furusaki, A.1
Watanabé, T.2
Matsumoto, T.3
Yanagiya, M.4
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18
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0034618262
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(c) See also ref 10
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(b) Kocienski, P.; Narquizian, R.; Raubo, P.; Smith, C.; Farrugia, L. J.; Muir, K.; Boyle, F. T. J. Chem. Soc., Perkin Trans. 1 2000, 2357-2384. (c) See also ref 10.
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(2000)
J. Chem. Soc., Perkin Trans. 1
, pp. 2357-2384
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Kocienski, P.1
Narquizian, R.2
Raubo, P.3
Smith, C.4
Farrugia, L.J.5
Muir, K.6
Boyle, F.T.7
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19
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3042852073
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note
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SAR studies have revealed that a 5S,8S absolute configuration is required for the potent cytotoxicity observed for analogous pederin-like compounds (see Figure 1 for numbering and ref 10).
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-
-
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20
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0035009212
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(a) All reported members of the pederin family possess optical rotations ranging between [α] = +22 (onnamide F: Vuong, D.; Capon, R. J.; Lacey, E.; Gill, J. H.; Heiland, K.; Friedel, T. J. Nat. Prod. 2001, 64, 640-642) and [α] = +172 (theopederin C: Fusetani, N.; Sugawara, T.; Matsunaga, S. J. Org. Chem. 1992, 57, 3828-3832). (b) See Table S1 for the optical rotations for all pederin metabolites.
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J. Nat. Prod.
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Vuong, D.1
Capon, R.J.2
Lacey, E.3
Gill, J.H.4
Heiland, K.5
Friedel, T.6
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21
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0026753195
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(b) See Table S1 for the optical rotations for all pederin metabolites
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(a) All reported members of the pederin family possess optical rotations ranging between [α] = +22 (onnamide F: Vuong, D.; Capon, R. J.; Lacey, E.; Gill, J. H.; Heiland, K.; Friedel, T. J. Nat. Prod. 2001, 64, 640-642) and [α] = +172 (theopederin C: Fusetani, N.; Sugawara, T.; Matsunaga, S. J. Org. Chem. 1992, 57, 3828-3832). (b) See Table S1 for the optical rotations for all pederin metabolites.
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(1992)
J. Org. Chem.
, vol.57
, pp. 3828-3832
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Fusetani, N.1
Sugawara, T.2
Matsunaga, S.3
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23
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0347717826
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(b) Piel, J.; Wen, G.; Platzer, M.; Hui, D. ChemBioChem 2004, 5, 93-98.
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Piel, J.1
Wen, G.2
Platzer, M.3
Hui, D.4
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24
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3042768824
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note
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The name psymberin is derived from Psammocinia + symbiont + pederin in view of its relationship to the pederin family.
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25
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0036637673
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Bioassay procedures are described in Valeriote, F.; Grieshaber, C. K.; Media, J.; Pietraszkewicz, H.; Hoffmann, J.; Pan, M.; McLaughlin, S. J. Exp. Ther. Oncol. 2002, 2, 228-236.
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J. Exp. Ther. Oncol.
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Valeriote, F.1
Grieshaber, C.K.2
Media, J.3
Pietraszkewicz, H.4
Hoffmann, J.5
Pan, M.6
McLaughlin, S.7
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0027285228
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(b) Kobayashi, J.; Itagaki, F.; Shigemori, H.; Sasaki, T. J. Nat. Prod. 1993, 56, 976-981.
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Kobayashi, J.1
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Sasaki, T.4
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0034092265
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(c) West, L. M.; Northcote, P. T.; Hood, K. A.; Miller, J. H.; Page, M. J. J. Nat. Prod. 2000, 63, 707-709.
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West, L.M.1
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Page, M.J.5
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(d) Hood, K. A.; West, L. M.; Northcote, P. T.; Berridge, M. V.; Miller, J. H. Apoptosis 2001, 6, 207-219.
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Miller, J.H.5
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0036163358
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(e) Paul, G. K.; Gunasekera, S. P.; Longley, R. E.; Pomponi, S. A. J. Nat. Prod. 2002, 65, 59-61.
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