메뉴 건너뛰기




Volumn 121, Issue 5, 1999, Pages 1098-1099

Total synthesis of luzopeptins A-C [6]

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ANTINEOPLASTIC ANTIBIOTIC; LUZOPEPTIN; LUZOPEPTIN A; LUZOPEPTIN B; LUZOPEPTIN C; UNCLASSIFIED DRUG;

EID: 0033540632     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983925b     Document Type: Letter
Times cited : (51)

References (42)
  • 2
    • 0019457091 scopus 로고
    • Arnold, E.; Clardy, J. J. Am. Chem. Soc. 1981, 103, 1243. Konishi, M.; Ohkuma, H.; Sakai, F.; Tsuno, T.; Koshiyama, H.; Naito, T.; Kawaguchi, H. J. Am. Chem. Soc. 1981, 103, 1241.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 1243
    • Arnold, E.1    Clardy, J.2
  • 6
    • 0024791787 scopus 로고
    • Matson, J. A.; Bush, J. A. J. Antibiot. 1989, 42, 1763. Matson, J. A.; Colson, K. L.; Belofsky, G. N.; Bleiberg, B. B. J. Antibiot. 1993, 46, 162.
    • (1989) J. Antibiot. , vol.42 , pp. 1763
    • Matson, J.A.1    Bush, J.A.2
  • 8
    • 0027139933 scopus 로고
    • Total synthesis of sandramycin: Boger, D. L.; Chen, J.-H. J. Am. Chem. Soc. 1993, 115, 11624. Boger, D. L.; Chen, J.-H.; Saionz, K. W. J. Am. Chem. Soc. 1996, 118, 1629.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 11624
    • Boger, D.L.1    Chen, J.-H.2
  • 9
    • 0030012287 scopus 로고    scopus 로고
    • Total synthesis of sandramycin: Boger, D. L.; Chen, J.-H. J. Am. Chem. Soc. 1993, 115, 11624. Boger, D. L.; Chen, J.-H.; Saionz, K. W. J. Am. Chem. Soc. 1996, 118, 1629.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1629
    • Boger, D.L.1    Chen, J.-H.2    Saionz, K.W.3
  • 12
    • 0019206031 scopus 로고
    • Huang, C.-H.; Mong, S.; Crooke, S. T. Biochemistry 1980, 19, 5537. Huang, C.-H.; Prestayko, A. W.; Crooke, S. T. Biochemistry 1982, 21, 3704. Huang, C.-H.; Mirabelli, C. K.; Mong, S.; Crooke, S. T. Cancer Res. 1983, 43, 2718. Huang, C.-H.; Crooke, S. T. Cancer Res. 1985, 45, 3768.
    • (1980) Biochemistry , vol.19 , pp. 5537
    • Huang, C.-H.1    Mong, S.2    Crooke, S.T.3
  • 13
    • 0020385470 scopus 로고
    • Huang, C.-H.; Mong, S.; Crooke, S. T. Biochemistry 1980, 19, 5537. Huang, C.-H.; Prestayko, A. W.; Crooke, S. T. Biochemistry 1982, 21, 3704. Huang, C.-H.; Mirabelli, C. K.; Mong, S.; Crooke, S. T. Cancer Res. 1983, 43, 2718. Huang, C.-H.; Crooke, S. T. Cancer Res. 1985, 45, 3768.
    • (1982) Biochemistry , vol.21 , pp. 3704
    • Huang, C.-H.1    Prestayko, A.W.2    Crooke, S.T.3
  • 14
    • 0020526851 scopus 로고
    • Huang, C.-H.; Mong, S.; Crooke, S. T. Biochemistry 1980, 19, 5537. Huang, C.-H.; Prestayko, A. W.; Crooke, S. T. Biochemistry 1982, 21, 3704. Huang, C.-H.; Mirabelli, C. K.; Mong, S.; Crooke, S. T. Cancer Res. 1983, 43, 2718. Huang, C.-H.; Crooke, S. T. Cancer Res. 1985, 45, 3768.
    • (1983) Cancer Res. , vol.43 , pp. 2718
    • Huang, C.-H.1    Mirabelli, C.K.2    Mong, S.3    Crooke, S.T.4
  • 15
    • 0021931261 scopus 로고
    • Huang, C.-H.; Mong, S.; Crooke, S. T. Biochemistry 1980, 19, 5537. Huang, C.-H.; Prestayko, A. W.; Crooke, S. T. Biochemistry 1982, 21, 3704. Huang, C.-H.; Mirabelli, C. K.; Mong, S.; Crooke, S. T. Cancer Res. 1983, 43, 2718. Huang, C.-H.; Crooke, S. T. Cancer Res. 1985, 45, 3768.
    • (1985) Cancer Res. , vol.45 , pp. 3768
    • Huang, C.-H.1    Crooke, S.T.2
  • 17
    • 0025021846 scopus 로고
    • Fox, K. R.; Davies, H.; Adams, G. R.; Portugal, J.; Waring, M. J. Nucl. Acids Res. 1988, 16, 2489. Fox, K. R.; Woolley, C. Biochem. Pharmacol. 1990, 39, 941.
    • (1990) Biochem. Pharmacol. , vol.39 , pp. 941
    • Fox, K.R.1    Woolley, C.2
  • 19
    • 0025858691 scopus 로고
    • Zhang, X.; Patel, D. J. Biochemistry 1991, 30, 4026. Leroy, J. L.; Gao, X.; Misra, V.; Gueron, M.; Patel, D. J. Biochemistry 1992, 31, 1407.
    • (1991) J. Biochemistry , vol.30 , pp. 4026
    • Zhang, X.1    Patel, D.2
  • 22
    • 0022588568 scopus 로고
    • Rose, W. C.; Schurig, J. E.; Huftalen, J. B.; Bradner, W. T. Cancer Res. 1983, 43, 1504. Huang, C.-H.; Crooke, S. T. Anti-cancer Drug Des. 1986, 1, 87.
    • (1986) Anti-cancer Drug Des. , vol.1 , pp. 87
    • Huang, C.-H.1    Crooke, S.T.2
  • 26
    • 0009720059 scopus 로고
    • Hughes, P.; Clardy, J. J. Org. Chem. 1989, 54, 3260. Greek, C.; Bischoff, L.; Genet, J. P. Tetrahedron: Asymmetry 1995, 6, 1989.
    • (1989) J. Org. Chem. , vol.54 , pp. 3260
    • Hughes, P.1    Clardy, J.2
  • 28
    • 0024345612 scopus 로고
    • Ciufolini, M. A.; Swaminathan, S. Tetrahedron Lett. 1989, 30, 3027. Ciufolini, M. A.; Xi, N. J. Chem. Soc., Chem. Commun. 1994, 1867. Xi, N.; Ciufolini, M. A. Tetrahedron Lett. 1995, 36, 6595. Ciufolini, M.; Xi, N. J. Org. Chem. 1997, 62, 2320. Xi, N.; Alemany, L. B.; Ciufolini, M. A. J. Am. Chem. Soc. 1998, 120, 80.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 3027
    • Ciufolini, M.A.1    Swaminathan, S.2
  • 29
    • 0028142554 scopus 로고
    • Ciufolini, M. A.; Swaminathan, S. Tetrahedron Lett. 1989, 30, 3027. Ciufolini, M. A.; Xi, N. J. Chem. Soc., Chem. Commun. 1994, 1867. Xi, N.; Ciufolini, M. A. Tetrahedron Lett. 1995, 36, 6595. Ciufolini, M.; Xi, N. J. Org. Chem. 1997, 62, 2320. Xi, N.; Alemany, L. B.; Ciufolini, M. A. J. Am. Chem. Soc. 1998, 120, 80.
    • (1994) J. Chem. Soc., Chem. Commun. , pp. 1867
    • Ciufolini, M.A.1    Xi, N.2
  • 30
    • 85012099807 scopus 로고
    • Ciufolini, M. A.; Swaminathan, S. Tetrahedron Lett. 1989, 30, 3027. Ciufolini, M. A.; Xi, N. J. Chem. Soc., Chem. Commun. 1994, 1867. Xi, N.; Ciufolini, M. A. Tetrahedron Lett. 1995, 36, 6595. Ciufolini, M.; Xi, N. J. Org. Chem. 1997, 62, 2320. Xi, N.; Alemany, L. B.; Ciufolini, M. A. J. Am. Chem. Soc. 1998, 120, 80.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 6595
    • Xi, N.1    Ciufolini, M.A.2
  • 31
    • 0030927251 scopus 로고    scopus 로고
    • Ciufolini, M. A.; Swaminathan, S. Tetrahedron Lett. 1989, 30, 3027. Ciufolini, M. A.; Xi, N. J. Chem. Soc., Chem. Commun. 1994, 1867. Xi, N.; Ciufolini, M. A. Tetrahedron Lett. 1995, 36, 6595. Ciufolini, M.; Xi, N. J. Org. Chem. 1997, 62, 2320. Xi, N.; Alemany, L. B.; Ciufolini, M. A. J. Am. Chem. Soc. 1998, 120, 80.
    • (1997) J. Org. Chem. , vol.62 , pp. 2320
    • Ciufolini, M.1    Xi, N.2
  • 32
    • 0032515431 scopus 로고    scopus 로고
    • Ciufolini, M. A.; Swaminathan, S. Tetrahedron Lett. 1989, 30, 3027. Ciufolini, M. A.; Xi, N. J. Chem. Soc., Chem. Commun. 1994, 1867. Xi, N.; Ciufolini, M. A. Tetrahedron Lett. 1995, 36, 6595. Ciufolini, M.; Xi, N. J. Org. Chem. 1997, 62, 2320. Xi, N.; Alemany, L. B.; Ciufolini, M. A. J. Am. Chem. Soc. 1998, 120, 80.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 80
    • Xi, N.1    Alemany, L.B.2    Ciufolini, M.A.3
  • 35
    • 0001589756 scopus 로고
    • The crystallinity of 10 provided the occasion to ensure pure material free of the isomer 9 as well as any unnatural enantiomer (recrystallization, EtOAc-hexane) was enlisted in the subsequent steps
    • Roush, W. R.; Adam, M. A. J. Org. Chem. 1985, 50, 3752. The crystallinity of 10 provided the occasion to ensure pure material free of the isomer 9 as well as any unnatural enantiomer (recrystallization, EtOAc-hexane) was enlisted in the subsequent steps.
    • (1985) J. Org. Chem. , vol.50 , pp. 3752
    • Roush, W.R.1    Adam, M.A.2
  • 36
    • 0345350248 scopus 로고    scopus 로고
    • note
    • EDCI = 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOAt = 1-hydroxy-7-azabenzotriazole; DCC = 1,3-dicyclohexylcarbodiimide.
  • 38
    • 0344056652 scopus 로고    scopus 로고
    • note
    • 16-18 gave the diol (12-42%), and variable amounts of the mono OTBS product (10-28%) and an elimination product (37-65%) derived from loss of one of the L-Htp hydroxy groups.
  • 40
    • 0345350247 scopus 로고    scopus 로고
    • note
    • 2O 3/1/1, 23°C, 10 h (70%).
  • 42
    • 0344918997 scopus 로고    scopus 로고
    • Altering the length of time exposed to the hydrolysis conditions alters the relative amounts of 1-3 obtained
    • Altering the length of time exposed to the hydrolysis conditions alters the relative amounts of 1-3 obtained.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.