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Volumn 10, Issue 21, 2008, Pages 5087-5090

Stereocontrolled access to isoprostanes via a bicyclo[3.3.0]octene framework

Author keywords

[No Author keywords available]

Indexed keywords

FUSED HETEROCYCLIC RINGS; ISOPROSTANE DERIVATIVE; OCTANE;

EID: 58149173869     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802104z     Document Type: Article
Times cited : (76)

References (38)
  • 8
    • 42149158973 scopus 로고    scopus 로고
    • We recently reported a strategy to access E-type isoprostane isomers: Pinot, E, Guy, A, Fournial, A, Balas, L, Rossi, J. C, Durand, T. J. Org. Chem. 2008, 73, 3063
    • We recently reported a strategy to access E-type isoprostane isomers: Pinot, E.; Guy, A.; Fournial, A.; Balas, L.; Rossi, J. C.; Durand, T. J. Org. Chem. 2008, 73, 3063.
  • 11
  • 27
    • 60949103213 scopus 로고    scopus 로고
    • The ee's were determined by converting alcohols into their corresponding 2,4-dinitrobenzoate derivatives and by chiral HPLC analysis (see the Supporting Information).
    • The ee's were determined by converting alcohols into their corresponding 2,4-dinitrobenzoate derivatives and by chiral HPLC analysis (see the Supporting Information).
  • 29
    • 37049070648 scopus 로고    scopus 로고
    • Enone 5 was previously obtained in three steps from 4 by palladium-induced oxidation of the silyl enol ether obtained from the corresponding ketone in 55% yield; see: Parkes, K. E. B.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1988, 1119.
    • Enone 5 was previously obtained in three steps from 4 by palladium-induced oxidation of the silyl enol ether obtained from the corresponding ketone in 55% yield; see: Parkes, K. E. B.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1988, 1119.
  • 31
    • 84985279173 scopus 로고    scopus 로고
    • The stereochemistry of cis- and trans-1,3-diols 8a was confirmed by NMR experiments and by reported NMR data of trans-8a; see: Weinges, K.; Haremsa, S. Liebigs Ann. Chem. 1987, 679.
    • The stereochemistry of cis- and trans-1,3-diols 8a was confirmed by NMR experiments and by reported NMR data of trans-8a; see: Weinges, K.; Haremsa, S. Liebigs Ann. Chem. 1987, 679.
  • 32
    • 0029069807 scopus 로고    scopus 로고
    • It is reported that oxidation of diols by IBX afforded only lactols. For 1,4-diol to lactol oxidation by IBX, see: Corey, E. J.; Palani, A. Tetrahedron Lett. 1995, 36, 3485.
    • It is reported that oxidation of diols by IBX afforded only lactols. For 1,4-diol to lactol oxidation by IBX, see: Corey, E. J.; Palani, A. Tetrahedron Lett. 1995, 36, 3485.
  • 34
    • 0027944734 scopus 로고    scopus 로고
    • 2tIsoP 1 based on an approach developed by Rokach; see: Hwang, S. W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829.
    • 2tIsoP 1 based on an approach developed by Rokach; see: Hwang, S. W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829.
  • 35
    • 60949107979 scopus 로고    scopus 로고
    • Two side products were also isolated; a coeluting compound with 16 attributed to the E isomer and a compound corresponding to a silyl migration to the primary alcohol (see the Supporting Information).
    • Two side products were also isolated; a coeluting compound with 16 attributed to the E isomer and a compound corresponding to a silyl migration to the primary alcohol (see the Supporting Information).
  • 36
    • 60949087699 scopus 로고    scopus 로고
    • Absolute configurations were determinated after completion of the synthesis to known 15-F2t-ISoP 1 and its 15-epimer and by NMR correlation of known 17a see ref 23
    • 2t-ISoP 1 and its 15-epimer and by NMR correlation of known 17a (see ref 23).
  • 38
    • 60949086085 scopus 로고    scopus 로고
    • Yield given from a 1:1 mixture 17a and 17b after separation of triol epimers (see the Supporting Information).
    • Yield given from a 1:1 mixture 17a and 17b after separation of triol epimers (see the Supporting Information).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.