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10144244115
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in press
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Boger, D. L.; Goldberg, J. A.; McKie, J. A. Bioorg. Med. Chem. Lett., in press. Boger, D. L.; McKie, J. A.; Nishi, T.; Ogiku, T. J. Am. Chem. Soc. Submitted.
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Boger, D.L.1
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10144220794
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Submitted
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Boger, D. L.; Goldberg, J. A.; McKie, J. A. Bioorg. Med. Chem. Lett., in press. Boger, D. L.; McKie, J. A.; Nishi, T.; Ogiku, T. J. Am. Chem. Soc. Submitted.
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J. Am. Chem. Soc.
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Boger, D.L.1
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Nishi, T.3
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112
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10144260779
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note
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44 and suggests that the ambiguous experimental basis for this proposal be reexamined.
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113
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10144231576
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note
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The author has deposited the atomic coordinates for this structure with the Cambridge Crystallographic Data Centre, and the coordinates may be obtained upon request from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
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114
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0000063791
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Martin, D. G.; Kelly, R. C.; Watt, W.; Wienienski, N.; Mizsak, S. A.; Nielsen, J. W.; Prairie, M. D. J. Org. Chem. 1988, 53, 4610.
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Mizsak, S.A.5
Nielsen, J.W.6
Prairie, M.D.7
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115
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2942583333
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Bond lengths of 1.464-1.447 and 1.553-1.552 Å for the adjacent and opposite bonds have been established for symmetrical difluorocyclopropanes by microwave spectroscopy or X-ray versus cyclopropane itself (1.514 Å). X-ray: Dolbier, W. R., Jr.; Odaniec, M.: Gomulka, E.; Jaskolski, M.; Koroniak, H. Tetrahedron 1984, 40, 3945. Dolbier, W. R., Jr.; Odaniec, M.; Jaskolski, M.; Koroniak, H. J. Mol. Struct. 1986, 147, 155. Microwave spectroscopy: Parretta, A. T.; Laurie, V. W. J. Chem. Phys. 1975, 62, 2463. Computational studies: Deakyne, C. A.; Allen, L. C.; Craig, N. C. J. Am. Chem. Soc. 1977, 99, 3845. Durmaz, S.; Kollmar. H. J. Am. Chem. Soc. 1980, 102, 6942. Clark, T.; Spitznagel, G. W.; Klose, R.; Schleyer, P. von R. J. Am. Chem. Soc. 1984, 106, 4412. Boggs, J. E.; Fan, K. Acta Chem. Scand. 1988, A42, 595.
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(1984)
Tetrahedron
, vol.40
, pp. 3945
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Dolbier Jr., W.R.1
Odaniec, M.2
Gomulka, E.3
Jaskolski, M.4
Koroniak, H.5
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116
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10144229485
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-
Bond lengths of 1.464-1.447 and 1.553-1.552 Å for the adjacent and opposite bonds have been established for symmetrical difluorocyclopropanes by microwave spectroscopy or X-ray versus cyclopropane itself (1.514 Å). X-ray: Dolbier, W. R., Jr.; Odaniec, M.: Gomulka, E.; Jaskolski, M.; Koroniak, H. Tetrahedron 1984, 40, 3945. Dolbier, W. R., Jr.; Odaniec, M.; Jaskolski, M.; Koroniak, H. J. Mol. Struct. 1986, 147, 155. Microwave spectroscopy: Parretta, A. T.; Laurie, V. W. J. Chem. Phys. 1975, 62, 2463. Computational studies: Deakyne, C. A.; Allen, L. C.; Craig, N. C. J. Am. Chem. Soc. 1977, 99, 3845. Durmaz, S.; Kollmar. H. J. Am. Chem. Soc. 1980, 102, 6942. Clark, T.; Spitznagel, G. W.; Klose, R.; Schleyer, P. von R. J. Am. Chem. Soc. 1984, 106, 4412. Boggs, J. E.; Fan, K. Acta Chem. Scand. 1988, A42, 595.
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Dolbier Jr., W.R.1
Odaniec, M.2
Jaskolski, M.3
Koroniak, H.4
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117
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-
10144255344
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-
Bond lengths of 1.464-1.447 and 1.553-1.552 Å for the adjacent and opposite bonds have been established for symmetrical difluorocyclopropanes by microwave spectroscopy or X-ray versus cyclopropane itself (1.514 Å). X-ray: Dolbier, W. R., Jr.; Odaniec, M.: Gomulka, E.; Jaskolski, M.; Koroniak, H. Tetrahedron 1984, 40, 3945. Dolbier, W. R., Jr.; Odaniec, M.; Jaskolski, M.; Koroniak, H. J. Mol. Struct. 1986, 147, 155. Microwave spectroscopy: Parretta, A. T.; Laurie, V. W. J. Chem. Phys. 1975, 62, 2463. Computational studies: Deakyne, C. A.; Allen, L. C.; Craig, N. C. J. Am. Chem. Soc. 1977, 99, 3845. Durmaz, S.; Kollmar. H. J. Am. Chem. Soc. 1980, 102, 6942. Clark, T.; Spitznagel, G. W.; Klose, R.; Schleyer, P. von R. J. Am. Chem. Soc. 1984, 106, 4412. Boggs, J. E.; Fan, K. Acta Chem. Scand. 1988, A42, 595.
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J. Chem. Phys.
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Parretta, A.T.1
Laurie, V.W.2
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10144260156
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Bond lengths of 1.464-1.447 and 1.553-1.552 Å for the adjacent and opposite bonds have been established for symmetrical difluorocyclopropanes by microwave spectroscopy or X-ray versus cyclopropane itself (1.514 Å). X-ray: Dolbier, W. R., Jr.; Odaniec, M.: Gomulka, E.; Jaskolski, M.; Koroniak, H. Tetrahedron 1984, 40, 3945. Dolbier, W. R., Jr.; Odaniec, M.; Jaskolski, M.; Koroniak, H. J. Mol. Struct. 1986, 147, 155. Microwave spectroscopy: Parretta, A. T.; Laurie, V. W. J. Chem. Phys. 1975, 62, 2463. Computational studies: Deakyne, C. A.; Allen, L. C.; Craig, N. C. J. Am. Chem. Soc. 1977, 99, 3845. Durmaz, S.; Kollmar. H. J. Am. Chem. Soc. 1980, 102, 6942. Clark, T.; Spitznagel, G. W.; Klose, R.; Schleyer, P. von R. J. Am. Chem. Soc. 1984, 106, 4412. Boggs, J. E.; Fan, K. Acta Chem. Scand. 1988, A42, 595.
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Deakyne, C.A.1
Allen, L.C.2
Craig, N.C.3
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119
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33847085990
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-
Bond lengths of 1.464-1.447 and 1.553-1.552 Å for the adjacent and opposite bonds have been established for symmetrical difluorocyclopropanes by microwave spectroscopy or X-ray versus cyclopropane itself (1.514 Å). X-ray: Dolbier, W. R., Jr.; Odaniec, M.: Gomulka, E.; Jaskolski, M.; Koroniak, H. Tetrahedron 1984, 40, 3945. Dolbier, W. R., Jr.; Odaniec, M.; Jaskolski, M.; Koroniak, H. J. Mol. Struct. 1986, 147, 155. Microwave spectroscopy: Parretta, A. T.; Laurie, V. W. J. Chem. Phys. 1975, 62, 2463. Computational studies: Deakyne, C. A.; Allen, L. C.; Craig, N. C. J. Am. Chem. Soc. 1977, 99, 3845. Durmaz, S.; Kollmar. H. J. Am. Chem. Soc. 1980, 102, 6942. Clark, T.; Spitznagel, G. W.; Klose, R.; Schleyer, P. von R. J. Am. Chem. Soc. 1984, 106, 4412. Boggs, J. E.; Fan, K. Acta Chem. Scand. 1988, A42, 595.
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1842601941
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Bond lengths of 1.464-1.447 and 1.553-1.552 Å for the adjacent and opposite bonds have been established for symmetrical difluorocyclopropanes by microwave spectroscopy or X-ray versus cyclopropane itself (1.514 Å). X-ray: Dolbier, W. R., Jr.; Odaniec, M.: Gomulka, E.; Jaskolski, M.; Koroniak, H. Tetrahedron 1984, 40, 3945. Dolbier, W. R., Jr.; Odaniec, M.; Jaskolski, M.; Koroniak, H. J. Mol. Struct. 1986, 147, 155. Microwave spectroscopy: Parretta, A. T.; Laurie, V. W. J. Chem. Phys. 1975, 62, 2463. Computational studies: Deakyne, C. A.; Allen, L. C.; Craig, N. C. J. Am. Chem. Soc. 1977, 99, 3845. Durmaz, S.; Kollmar. H. J. Am. Chem. Soc. 1980, 102, 6942. Clark, T.; Spitznagel, G. W.; Klose, R.; Schleyer, P. von R. J. Am. Chem. Soc. 1984, 106, 4412. Boggs, J. E.; Fan, K. Acta Chem. Scand. 1988, A42, 595.
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Clark, T.1
Spitznagel, G.W.2
Klose, R.3
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121
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0037883523
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Bond lengths of 1.464-1.447 and 1.553-1.552 Å for the adjacent and opposite bonds have been established for symmetrical difluorocyclopropanes by microwave spectroscopy or X-ray versus cyclopropane itself (1.514 Å). X-ray: Dolbier, W. R., Jr.; Odaniec, M.: Gomulka, E.; Jaskolski, M.; Koroniak, H. Tetrahedron 1984, 40, 3945. Dolbier, W. R., Jr.; Odaniec, M.; Jaskolski, M.; Koroniak, H. J. Mol. Struct. 1986, 147, 155. Microwave spectroscopy: Parretta, A. T.; Laurie, V. W. J. Chem. Phys. 1975, 62, 2463. Computational studies: Deakyne, C. A.; Allen, L. C.; Craig, N. C. J. Am. Chem. Soc. 1977, 99, 3845. Durmaz, S.; Kollmar. H. J. Am. Chem. Soc. 1980, 102, 6942. Clark, T.; Spitznagel, G. W.; Klose, R.; Schleyer, P. von R. J. Am. Chem. Soc. 1984, 106, 4412. Boggs, J. E.; Fan, K. Acta Chem. Scand. 1988, A42, 595.
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84985560982
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Schwager, H.; Kruger, C.; Neidlein, R.; Wilke, G. Angew. Chem., Int. Ed. Engl. 1987, 26, 65. Thom, E.; Christensen, A, T. Acta Crystallogr., Sect. B: Struct. Sci. 1971, 27, 573. Christensen, A. T. Acta Crystallogr., Sect. B.; Struct. Sci. 1970, 26, 1519. Diaz, E.; Barrios, H.; Villena, R.; Toscano, R. A. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1991, 47, 2720 and 2723. Irngartinger, H.; Gries, S.; Klaus, P.; Gleiter, R. Chem. Ber. 1992, 125, 2503. Taguchi, T.; Shibuya, A.; Sasaki, H.; Endo, J.; Morikawa, T.; Shiro, M. Tetrahedron: Asymmetry 1994, 5, 1423.
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Schwager, H.; Kruger, C.; Neidlein, R.; Wilke, G. Angew. Chem., Int. Ed. Engl. 1987, 26, 65. Thom, E.; Christensen, A, T. Acta Crystallogr., Sect. B: Struct. Sci. 1971, 27, 573. Christensen, A. T. Acta Crystallogr., Sect. B.; Struct. Sci. 1970, 26, 1519. Diaz, E.; Barrios, H.; Villena, R.; Toscano, R. A. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1991, 47, 2720 and 2723. Irngartinger, H.; Gries, S.; Klaus, P.; Gleiter, R. Chem. Ber. 1992, 125, 2503. Taguchi, T.; Shibuya, A.; Sasaki, H.; Endo, J.; Morikawa, T.; Shiro, M. Tetrahedron: Asymmetry 1994, 5, 1423.
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Thom, E.1
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0014949907
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Schwager, H.; Kruger, C.; Neidlein, R.; Wilke, G. Angew. Chem., Int. Ed. Engl. 1987, 26, 65. Thom, E.; Christensen, A, T. Acta Crystallogr., Sect. B: Struct. Sci. 1971, 27, 573. Christensen, A. T. Acta Crystallogr., Sect. B.; Struct. Sci. 1970, 26, 1519. Diaz, E.; Barrios, H.; Villena, R.; Toscano, R. A. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1991, 47, 2720 and 2723. Irngartinger, H.; Gries, S.; Klaus, P.; Gleiter, R. Chem. Ber. 1992, 125, 2503. Taguchi, T.; Shibuya, A.; Sasaki, H.; Endo, J.; Morikawa, T.; Shiro, M. Tetrahedron: Asymmetry 1994, 5, 1423.
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Schwager, H.; Kruger, C.; Neidlein, R.; Wilke, G. Angew. Chem., Int. Ed. Engl. 1987, 26, 65. Thom, E.; Christensen, A, T. Acta Crystallogr., Sect. B: Struct. Sci. 1971, 27, 573. Christensen, A. T. Acta Crystallogr., Sect. B.; Struct. Sci. 1970, 26, 1519. Diaz, E.; Barrios, H.; Villena, R.; Toscano, R. A. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1991, 47, 2720 and 2723. Irngartinger, H.; Gries, S.; Klaus, P.; Gleiter, R. Chem. Ber. 1992, 125, 2503. Taguchi, T.; Shibuya, A.; Sasaki, H.; Endo, J.; Morikawa, T.; Shiro, M. Tetrahedron: Asymmetry 1994, 5, 1423.
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Barrios, H.2
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10144226529
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note
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Direct resolution of 17-19 on an HPLC ChiralCel OD column (0.46 × 25 cm, flow rate 0.7-1.0 mL/min) was examined and provides access to the optically active materials: 17, α = 1.18 (10-20% i-PrOH-hexane); 18, α = 1.09-1.05 (10-25% i-PrOH-hexane); 19. α = 1.12 (50% i-PrOH-hexane). However, the recovery was expected to be diminished due to the reactivity of the agents and consequently the preparative resolution of the agents was not pursued.
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note
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50 values for the natural enantiomers of 17-19 and 24 are 30, 70, 55 μM, and 18 nM, respectively, and consequently follow the trends between reactivity and cytotoxic potency even more closely.
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140
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0025980193
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Boger, D. L.; Munk, S. A.; Zarrinmayeh, H.; Ishizaki, T.; Haught, J.; Bina, M. Tetrahedron 1991, 47, 2661.
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Boger, D.L.1
Munk, S.A.2
Zarrinmayeh, H.3
Ishizaki, T.4
Haught, J.5
Bina, M.6
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Full experimental and characterization for 5-12 is provided in supporting information
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Full experimental and characterization for 5-12 is provided in supporting information.
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