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Volumn 74, Issue 5, 2009, Pages 1897-1916

Synthesis of a 35-member stereoisomer library of bistramide A: Evaluation of effects on actin state, cell cycle and tumor cell growth

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL EVALUATIONS; CANCER CELL LINES; CELL CYCLES; CROTYLSILANE REAGENTS; LEWIS ACIDS; NATURAL PRODUCTS; ORGANOSILANE; PEPTIDE COUPLINGS; TETRAHYDROPYRAN; TUMOR CELLS;

EID: 64249117392     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802269q     Document Type: Article
Times cited : (54)

References (137)
  • 44
    • 64249083559 scopus 로고    scopus 로고
    • For structural activity relationship studies on bistramide A, see ref 18
    • For structural activity relationship studies on bistramide A, see ref 18.
  • 64
    • 0033405872 scopus 로고    scopus 로고
    • For examples of Sharpless asymmetric epoxidation to generate epoxysilanes see: (a) Chauret, D. C, Chong, J. M, Ye, Q. Tetrahedron: Asymmetry 1999, 10, 3601
    • For examples of Sharpless asymmetric epoxidation to generate epoxysilanes see: (a) Chauret, D. C.; Chong, J. M.; Ye, Q. Tetrahedron: Asymmetry 1999, 10, 3601.
  • 66
    • 0001210758 scopus 로고
    • For an example of Shi epoxidation see
    • (c) Takeda, Y.; Matsumoto, T.; Sato, F. J. Org. Chem. 1986, 51, 4728. For an example of Shi epoxidation see:
    • (1986) J. Org. Chem , vol.51 , pp. 4728
    • Takeda, Y.1    Matsumoto, T.2    Sato, F.3
  • 68
    • 0000560497 scopus 로고    scopus 로고
    • For examples of kinetic resolutions see: (e) Carlier, P. R, Mungall, W. S, Schroder, G, Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 2978
    • For examples of kinetic resolutions see: (e) Carlier, P. R.; Mungall, W. S.; Schroder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 2978.
  • 70
    • 0001619975 scopus 로고    scopus 로고
    • 2 see: (g) Kobayashi, Y.; Uchiyama, H.; Kanbara, H.; Sato, F. J. Am. Chem. Soc. 1985, 107, 5541.
    • 2 see: (g) Kobayashi, Y.; Uchiyama, H.; Kanbara, H.; Sato, F. J. Am. Chem. Soc. 1985, 107, 5541.
  • 81
    • 64249170846 scopus 로고    scopus 로고
    • The enantiomeric excess was determined to be 98% for both 15a and ent-15a as observed with Chiralcel OD 99/1 (hexanes/IPA) at 1 mL/min (tR 35:92 for 15a and 45:17 for ent-15a).
    • The enantiomeric excess was determined to be 98% for both 15a and ent-15a as observed with Chiralcel OD 99/1 (hexanes/IPA) at 1 mL/min (tR 35:92 for 15a and 45:17 for ent-15a).
  • 82
    • 0028909387 scopus 로고    scopus 로고
    • For preparation of (2R,3R)-3-(triphenylsilyl)-2,3- epoxypropane-1-ol see: Raubo, P.; Wicha, J. Tetrahedron: Asymmetry 1995, 6, 577.
    • For preparation of (2R,3R)-3-(triphenylsilyl)-2,3- epoxypropane-1-ol see: Raubo, P.; Wicha, J. Tetrahedron: Asymmetry 1995, 6, 577.
  • 83
    • 84869275616 scopus 로고    scopus 로고
    • Elevated temperatures (-20, 0, and 25°C) under the described conditions for the (E)-vinylsilane did not provide the desired epoxide.
    • Elevated temperatures (-20, 0, and 25°C) under the described conditions for the (E)-vinylsilane did not provide the desired epoxide.
  • 84
    • 64249127149 scopus 로고    scopus 로고
    • A Shi epoxidation of 16 was also considered; however, literature precedent showed attenuated ee values for similar systems, see ref 32d for more information
    • A Shi epoxidation of 16 was also considered; however, literature precedent showed attenuated ee values for similar systems, see ref 32d for more information.
  • 85
    • 64249138143 scopus 로고    scopus 로고
    • Lipase AK Amano 20, Lipase PS Amano, and Lipase PS-D Amano were initially screened. Lipase PS-D was found to be superior.
    • Lipase AK "Amano" 20, Lipase PS "Amano", and Lipase PS-D "Amano" were initially screened. Lipase PS-D was found to be superior.
  • 86
    • 84869265542 scopus 로고    scopus 로고
    • R 5:03 for 15b and 7.08 for ent-15b).
    • R 5:03 for 15b and 7.08 for ent-15b).
  • 88
    • 64249095551 scopus 로고    scopus 로고
    • Decomposition of cis and trans epoxide acids was noticed upon prolonged storage or column chromatography.
    • Decomposition of cis and trans epoxide acids was noticed upon prolonged storage or column chromatography.
  • 89
    • 64249098618 scopus 로고    scopus 로고
    • During the course of oxidation, the reaction solution became a dark green color with a black suspension, suggesting an inactive catalytic system. To drive the reaction to completion, catalyst loading was increased and extended reaction times were explored with little success. Only a reset of the catalytic system provided full conversion
    • During the course of oxidation, the reaction solution became a dark green color with a black suspension, suggesting an inactive catalytic system. To drive the reaction to completion, catalyst loading was increased and extended reaction times were explored with little success. Only a reset of the catalytic system provided full conversion.
  • 99
    • 2742569677 scopus 로고    scopus 로고
    • It has been suggested that silicon prefers an axial orientation for both electronic and steric reasons but may still eliminate even without optimal orbital overlap. For a detailed discussion and relevant examples see: Lambert, J. B. Tetrahedron 1990, 46, 2677
    • It has been suggested that silicon prefers an axial orientation for both electronic and steric reasons but may still eliminate even without optimal orbital overlap. For a detailed discussion and relevant examples see: Lambert, J. B. Tetrahedron 1990, 46, 2677.
  • 100
    • 0030914643 scopus 로고    scopus 로고
    • Intramolecular silyl-modified Sakurai condensations of vinylsilanes suggest allylic strain plays a role in stereochemical outcome: Marko, I. E, Dobbs, A. P, Seheirmann, V. Chellé, F, Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899
    • Intramolecular silyl-modified Sakurai condensations of vinylsilanes suggest allylic strain plays a role in stereochemical outcome: Marko, I. E.; Dobbs, A. P.; Seheirmann, V. Chellé, F.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899.
  • 101
    • 0034966749 scopus 로고    scopus 로고
    • It is conceivable that an aronia-Cope rearrangement could play a role in the stereochemical outcome of these reactions; however, no byproducts from this pathway were observed. For an example of oxonia-Cope rearrangements in allyl systems, see: Roush, W. R.; Dilley, G. J. Synlett 2001, 955.
    • It is conceivable that an aronia-Cope rearrangement could play a role in the stereochemical outcome of these reactions; however, no byproducts from this pathway were observed. For an example of oxonia-Cope rearrangements in allyl systems, see: Roush, W. R.; Dilley, G. J. Synlett 2001, 955.
  • 106
    • 64249153570 scopus 로고    scopus 로고
    • The homoallylic substrates were converted to 1,1-dimethyl acetonides in a three-step sequence
    • The homoallylic substrates were converted to 1,1-dimethyl acetonides in a three-step sequence.
  • 115
    • 0037034362 scopus 로고    scopus 로고
    • For a previous example of spirocvclization in the presence of DDQ see
    • For a previous example of spirocvclization in the presence of DDQ see: Paterson, I.; Chen, D. Y.-K.; Franklin, A. S. Org. Lett. 2002, 4, 391.
    • (2002) Org. Lett , vol.4 , pp. 391
    • Paterson, I.1    Chen, D.Y.-K.2    Franklin, A.S.3
  • 116
    • 64249114450 scopus 로고    scopus 로고
    • Anhydrous conditions resulted in no reactions while using phosphate buffer (pH 7) provided 19% yield of the desired spirocycle.
    • Anhydrous conditions resulted in no reactions while using phosphate buffer (pH 7) provided 19% yield of the desired spirocycle.
  • 117
    • 64249158653 scopus 로고    scopus 로고
    • Conditions found in Table 3 were also applied to 44 with little success.
    • Conditions found in Table 3 were also applied to 44 with little success.
  • 121
    • 0031584948 scopus 로고    scopus 로고
    • '(70) Onoda, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1997, 38, 1443.
    • '(70) Onoda, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett. 1997, 38, 1443.
  • 122
    • 84986955199 scopus 로고    scopus 로고
    • 2) in the DDQ oxidation of silyl enol ethers has also been noted, see: (a) Fleming, I.; Paterson, I. Synthesis 1979, 736.
    • 2) in the DDQ oxidation of silyl enol ethers has also been noted, see: (a) Fleming, I.; Paterson, I. Synthesis 1979, 736.
  • 130
    • 3943096588 scopus 로고    scopus 로고
    • Charge-transfer complexes with other nitrogen heterocycles including imidazoles and pyrimidines have been reported, see: (a) Salman, H. M. A, Rabie, U. M, Abd-Alla, E. M. Can. J. Anal. Sci. Spectrosc. 2004, 49, 1
    • Charge-transfer complexes with other nitrogen heterocycles including imidazoles and pyrimidines have been reported, see: (a) Salman, H. M. A.; Rabie, U. M.; Abd-Alla, E. M. Can. J. Anal. Sci. Spectrosc. 2004, 49, 1.
  • 133
    • 0026516860 scopus 로고
    • For a review of the Staudinger reaction see
    • For a review of the Staudinger reaction see: Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353.
    • (1992) Tetrahedron , vol.48 , pp. 1353
    • Gololobov, Y.G.1    Kasukhin, L.F.2
  • 134
    • 64249172173 scopus 로고    scopus 로고
    • The unknown product was obtained as a mixture of isomers with a loss of C2-C3 olefin. We were unable to separate the mixture for characterization.
    • The unknown product was obtained as a mixture of isomers with a loss of C2-C3 olefin. We were unable to separate the mixture for characterization.


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