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Volumn 124, Issue 41, 2002, Pages 12078-12079

Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOGENESIS INHIBITOR; AZASPIRENE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

EID: 0037120884     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0276826     Document Type: Article
Times cited : (73)

References (37)
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    • (b) Risau, W. Nature 1997, 386, 671.
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    • note
    • For the determination of ee, see the Supporting Information.
  • 21
    • 84926230308 scopus 로고    scopus 로고
    • note
    • Ketene silyl acetal 7 was obtained as a single isomer, the geometry of which has not been determined.
  • 22
    • 0028608155 scopus 로고
    • 3 is an effective Lewis acid in Mukaiyama aldol reaction of a silylketene acetal derived from di-tert-butyl-(2S,3S)-1,4-dioxaspiro-[4.4]nonane-2,3-dicarboxylate. Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111; Evans, D. A.; Trotter, B. W.; Barrow, J. C. Tetrahedron 1997, 53, 8779.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 12111
    • Evans, D.A.1    Barrow, J.C.2    Leighton, J.L.3    Robichaud, A.J.4    Sefkow, M.5
  • 23
    • 0030803002 scopus 로고    scopus 로고
    • 3 is an effective Lewis acid in Mukaiyama aldol reaction of a silylketene acetal derived from di-tert-butyl-(2S,3S)- 1,4-dioxaspiro-[4.4]nonane-2,3-dicarboxylate. Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111; Evans, D. A.; Trotter, B. W.; Barrow, J. C. Tetrahedron 1997, 53, 8779.
    • (1997) Tetrahedron , vol.53 , pp. 8779
    • Evans, D.A.1    Trotter, B.W.2    Barrow, J.C.3
  • 24
    • 0035532076 scopus 로고    scopus 로고
    • 2 as an effective Lewis acid, see: (a) Fujisawa, H.; Sasaki, Y.; Mukaiyama, T. Chem. Lett. 2001, 190.(b) Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392. (c) Sibi, M. P.; Sausker, J. B. J. Am. Chem. Soc. 2002, 124, 984.
    • (2001) Chem. Lett. , pp. 190
    • Fujisawa, H.1    Sasaki, Y.2    Mukaiyama, T.3
  • 25
    • 0037160423 scopus 로고    scopus 로고
    • (a) Fujisawa, H.; Sasaki, Y.; Mukaiyama, T. Chem. Lett. 2001, 190.(b) Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392. (c) Sibi, M. P.; Sausker, J. B. J. Am. Chem. Soc. 2002, 124, 984.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 392
    • Evans, D.A.1    Tedrow, J.S.2    Shaw, J.T.3    Downey, C.W.4
  • 26
    • 0037065709 scopus 로고    scopus 로고
    • (a) Fujisawa, H.; Sasaki, Y.; Mukaiyama, T. Chem. Lett. 2001, 190.(b) Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392. (c) Sibi, M. P.; Sausker, J. B. J. Am. Chem. Soc. 2002, 124, 984.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 984
    • Sibi, M.P.1    Sausker, J.B.2
  • 27
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    • note
    • 3, Z = 2 R1 = 0.0698 for 1 > 2.0σ, wR2 = 0.1713 for all data (5002 reflections). The details are supplied as Supporting Information (Figure SI).
  • 28
    • 84926230842 scopus 로고    scopus 로고
    • note
    • The geometry of the olefins was determined by NOESY experiment.
  • 35
    • 84926230717 scopus 로고    scopus 로고
    • note
    • 13C NMR analyses show that 15 exists in the 1,3-diketo form rather than the keto-enol form.
  • 36
    • 84926230199 scopus 로고    scopus 로고
    • note
    • The stereochemistry at C8 was confirmed by NOESY and difference NOE experiments, see Supporting Information.
  • 37
    • 84926230267 scopus 로고    scopus 로고
    • note
    • 16 was obtained in 94% yield from 15 by repeated treatment with thin-layer chromatography (TLC).


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