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Volumn 72, Issue 3, 2007, Pages 1027-1030

Synthesis of (±)-epi-stegobinone utilizing silacyclopropanes as synthetic intermediates

Author keywords

[No Author keywords available]

Indexed keywords

PLUSMN-1PRIMEEPI- STEGOBINONE; SILACYCLOPROPANE-DERIVED DIOL; SYNTHETIC INTERMEDIATES; TARGET-DIRECTED SYNTHESIS;

EID: 33846896658     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0620011     Document Type: Article
Times cited : (13)

References (43)
  • 7
    • 0018600199 scopus 로고    scopus 로고
    • The absolute configuration of stegobinone was determined by stereocontrolled synthesis: (a) Hoffmann, R. W.; Ladner, W. Tetrahedron Lett. 1979, 4653-4656.
    • The absolute configuration of stegobinone was determined by stereocontrolled synthesis: (a) Hoffmann, R. W.; Ladner, W. Tetrahedron Lett. 1979, 4653-4656.
  • 11
    • 45149140003 scopus 로고    scopus 로고
    • For syntheses of 1′-epi-stegobinone, see: (a) Ebata, T.; Koseki, K.; Shimazaki, K.; Kawakami, H.; Chuman, T.; Matsushita, H.; Mori, K. Heterocycles 1990, 31, 581-585.
    • For syntheses of 1′-epi-stegobinone, see: (a) Ebata, T.; Koseki, K.; Shimazaki, K.; Kawakami, H.; Chuman, T.; Matsushita, H.; Mori, K. Heterocycles 1990, 31, 581-585.
  • 21
    • 33846903224 scopus 로고    scopus 로고
    • Addition of the corresponding allylic silane, which would produce diol 9 after carbon-silicon bond oxidation, was not selective (58:42 dr).
    • Addition of the corresponding allylic silane, which would produce diol 9 after carbon-silicon bond oxidation, was not selective (58:42 dr).
  • 23
    • 33846938904 scopus 로고    scopus 로고
    • Both E and Z alkene isomers of the enol silane provided the same major product, as reported in ref 19.
    • Both E and Z alkene isomers of the enol silane provided the same major product, as reported in ref 19.
  • 34
    • 0025364262 scopus 로고    scopus 로고
    • Aldol reactions of Sn(II) enolates have demonstrated a preference for anti,syn products: Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866-868.
    • Aldol reactions of Sn(II) enolates have demonstrated a preference for anti,syn products: Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866-868.
  • 35
    • 84958315401 scopus 로고    scopus 로고
    • Syn,syn-stereochemistry has been obtained with β-siloxy titanium enolates: Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpí, F. J. Am. Chem. Soc. 1991, 113, 1047-1049.
    • Syn,syn-stereochemistry has been obtained with β-siloxy titanium enolates: Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpí, F. J. Am. Chem. Soc. 1991, 113, 1047-1049.
  • 39
    • 33846934091 scopus 로고    scopus 로고
    • When diol 9 was protected as the benzyl ether, a boron-mediated aldol reaction provided a 66:34 ratio of diastereomers.
    • When diol 9 was protected as the benzyl ether, a boron-mediated aldol reaction provided a 66:34 ratio of diastereomers.
  • 40
    • 33846898407 scopus 로고    scopus 로고
    • 9 was protected as an acetonide, a boron-mediated aldol reaction provided a 68:32 ratio of diastereomers
    • reaction
    • When diol 9 was protected as an acetonide, a boron-mediated aldol reaction provided a 68:32 ratio of diastereomers. Titanium and tin enolates provided no reaction.
    • Titanium and tin enolates provided
    • When diol1
  • 41
    • 33846907060 scopus 로고    scopus 로고
    • For a description of the general experimental methods, see the Supporting Information
    • For a description of the general experimental methods, see the Supporting Information.
  • 42
    • 33846937469 scopus 로고    scopus 로고
    • Although compounds 4, 5, 7, and 9 have been prepared previously ref 16, their synthesis has been optimized. The improved procedures are provided in the Supporting Information
    • Although compounds 4, 5, 7, and 9 have been prepared previously (ref 16), their synthesis has been optimized. The improved procedures are provided in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.