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Volumn 9, Issue 13, 2007, Pages 2557-2559

Enantioselective total synthesis of isishippuric acid B via intramolecular michael reaction

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DICARBOXYLIC ACID; ISISHIPPURIC ACID B; UNCLASSIFIED DRUG;

EID: 34547181292     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070956f     Document Type: Article
Times cited : (15)

References (20)
  • 8
    • 0000313688 scopus 로고    scopus 로고
    • For a concise construction of the quadranoid skeleton by a tandem radical cyclization-rearrangement sequence and its application to the syntehsis of (±)-suberosenone, see: Lee, H.-Y, Lim, B. G. Org. Lett. 2000, 2, 1951-1953
    • For a concise construction of the quadranoid skeleton by a tandem radical cyclization-rearrangement sequence and its application to the syntehsis of (±)-suberosenone, see: Lee, H.-Y.; Lim, B. G. Org. Lett. 2000, 2, 1951-1953.
  • 10
    • 0029934950 scopus 로고    scopus 로고
    • For structures and biological activities of related quadranoids, see: a
    • For structures and biological activities of related quadranoids, see: (a) Bokesch, H. R.; McKee, T. C.; Cardellina, J. H., II; Boyd, M. R. Tetrahedron Lett. 1996, 37, 3259-3262.
    • (1996) Tetrahedron Lett , vol.37 , pp. 3259-3262
    • Bokesch, H.R.1    McKee, T.C.2    Cardellina II, J.H.3    Boyd, M.R.4
  • 13
    • 0027972829 scopus 로고    scopus 로고
    • Our three-step synthetic route to 8 from commercially available (R)-citronellal (6) is operationally easy, low in cost, and therefore suitable for its large-scale production. For other methods to prepare 8 or its enantiomer, see: (a) McWilliams, J. C, Clardy, J. J. Am. Chem. Soc. 1994, 116, 8378-8379
    • Our three-step synthetic route to 8 from commercially available (R)-citronellal (6) is operationally easy, low in cost, and therefore suitable for its large-scale production. For other methods to prepare 8 or its enantiomer, see: (a) McWilliams, J. C.; Clardy, J. J. Am. Chem. Soc. 1994, 116, 8378-8379.
  • 16
    • 34547182842 scopus 로고    scopus 로고
    • 2 at -78°C, two silyl enol ethers [9 and its isomer, (R)-6-methyl-1-(triisopropylsilyl)oxy1,3-cycloheptadiene] were obtained in a ratio of 1:1.
    • 2 at -78°C, two silyl enol ethers [9 and its isomer, (R)-6-methyl-1-(triisopropylsilyl)oxy1,3-cycloheptadiene] were obtained in a ratio of 1:1.
  • 17
    • 34547216803 scopus 로고    scopus 로고
    • 2) was also unsuccessful.
    • 2) was also unsuccessful.
  • 18
    • 34547204463 scopus 로고    scopus 로고
    • Structure 15 is drawn as a conformer preferred for the Michael cyclization in the next step, and does not mean the real conformation of 15.
    • Structure 15 is drawn as a conformer preferred for the Michael cyclization in the next step, and does not mean the real conformation of 15.
  • 19
    • 34547194690 scopus 로고    scopus 로고
    • 2-Bu moiety and a geminal methyl group in the transition state leading from the (Z)-isomer to 16.
    • 2-Bu moiety and a geminal methyl group in the transition state leading from the (Z)-isomer to 16.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.