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Volumn 53, Issue 51, 1997, Pages 17335-17342

Strategic use of retro Diels-Alder reaction in the construction of β-carboxy-α-methylene-γ-lactones. Total synthesis of methylenolactocin and protolichesterinic acid

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; ANTINEOPLASTIC ANTIBIOTIC; PROTOLICHESTERINIC ACID; UNCLASSIFIED DRUG;

EID: 0030865419     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10157-0     Document Type: Article
Times cited : (35)

References (37)
  • 2
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    • i) For isolation and structure elucidation see: a) Zopf, W. Liebigs Ann. Chem. 1902, 324, 39, 1904, 336, 46.
    • (1902) Liebigs Ann. Chem. , vol.324 , pp. 39
    • Zopf, W.1
  • 3
    • 84977693859 scopus 로고
    • i) For isolation and structure elucidation see: a) Zopf, W. Liebigs Ann. Chem. 1902, 324, 39, 1904, 336, 46.
    • (1904) Liebigs Ann. Chem. , vol.336 , pp. 46
  • 5
    • 84858286617 scopus 로고
    • b) Asahina, Y.; Asano, M. J. Pharm. Soc. Jpn. 1927, 539, 1; Chem. Abstr. 1928, 22, 4470.
    • (1928) Chem. Abstr. , vol.22 , pp. 4470
  • 7
    • 0003842908 scopus 로고
    • CRC Press: Boca Raton, FL, and references cited therein
    • ii) For biological properties see: a) Berdy, J. Handbook of Antibiotic Compounds; CRC Press: Boca Raton, FL, 1982; Vol. IX and references cited therein.
    • (1982) Handbook of Antibiotic Compounds , vol.9
    • Berdy, J.1
  • 10
    • 85009870889 scopus 로고
    • c) Shibata, S; Miura, Y.; Sugimura, H.; Toyoizumi, Y. J. Pharm. Soc. Jpn. 1948, 68, 300; Chem Abstr., 1951, 45, 6691i.
    • (1951) Chem Abstr. , vol.45
  • 12
    • 4243992921 scopus 로고
    • d) Fujikawa, F.; Hitosa, Y.; Yamaoka, M.; Fujiwara, Y.; Nakazawa, S.; Omatsu, T.; Toyoda, T. Ibid. 1953, 73, 135.; Chem. Abstr. 1954, 48, 230a.
    • (1954) Chem. Abstr. , vol.48
  • 14
    • 25344477105 scopus 로고
    • e) Borkowski, B.; Wozniak, W.; Gertig, H.; Werakso, B. Diss. Pharm. 1964, 16, 189; Chem. Abstr. 1965, 62, 1995b.
    • (1965) Chem. Abstr. , vol.62
  • 16
    • 85036675146 scopus 로고
    • f) Sticher, O. Pharm. Acta. Helv. 1965, 40, 183; Chem. Abstr. 1965, 63, 8778d.
    • (1965) Chem. Abstr. , vol.63
  • 18
    • 0013791153 scopus 로고
    • g) Sticher, O; Pharm. Acta. Helv. 1965, 40, 385, .Chem. Abstr. 1965, 63, 12026c.
    • (1965) Chem. Abstr. , vol.63
  • 20
    • 0019210245 scopus 로고
    • h) Hirayama, T.; Fujikawa, F.; Kasahara, T.; Otsuka, M.; Nishida, N.; Mizuno, D. Yakugaku Zasshi 1980, 100, 755; Chem. Abstr. 1980, 93, 179563f.
    • (1980) Chem. Abstr. , vol.93
  • 34
    • 85082550403 scopus 로고
    • For an account of the use of retro Diels-Alder reaction in the synthesis of α-methylene lactones see: Ichihara, A. Synthesis 1987, 207.
    • (1987) Synthesis , pp. 207
    • Ichihara, A.1
  • 35
    • 85036675487 scopus 로고    scopus 로고
    • note
    • Part of the results had appeared as a preliminary communication. See ref. 3i
  • 36
    • 0030744068 scopus 로고    scopus 로고
    • A similar relief of eclipsing interaction between substituents through enolisation in a substituted cyclopentanone derivative has been observed. See: Haque, A.; Ghatak, A.; Ghosh, S.; Ghoshal, N. J. Org. Chem. 1997, 62, 5211.
    • (1997) J. Org. Chem. , vol.62 , pp. 5211
    • Haque, A.1    Ghatak, A.2    Ghosh, S.3    Ghoshal, N.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.