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Volumn 63, Issue 20, 1998, Pages 6774-6775

Total synthesis of clerocidin via a novel, enantioselective homoallenylboration methodology

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; ALLENE DERIVATIVE; BORONIC ACID DERIVATIVE; CLEROCIDIN; DITERPENOID; NATURAL PRODUCT; UNCLASSIFIED DRUG;

EID: 0032476076     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981331l     Document Type: Article
Times cited : (54)

References (28)
  • 9
    • 0030007125 scopus 로고    scopus 로고
    • Binaschi, M.; Zagotto, G.; Palumbo, M.; Zunico, F.; Farinosi, R.; Carpanico, G. Cancer Res. 1997, 57, 1710.
    • Sehested, M.; Jensen, P. B. Biochem. Pharmacol. 1996, 51, 879. Binaschi, M.; Zagotto, G.; Palumbo, M.; Zunico, F.; Farinosi, R.; Carpanico, G. Cancer Res. 1997, 57, 1710.
    • (1996) Biochem. Pharmacol. , vol.51 , pp. 879
    • Sehested, M.1    Jensen, P.B.2
  • 16
    • 33744643669 scopus 로고
    • The resulting l,3-butadienyl-2-carbinols are commonly used as DielsAlder dienes. For selected examples see: Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089. Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162.
    • (1991) Synthesis , vol.1089 , pp. 4162
    • Wender, P.A.1    Tebbe, M.J.2
  • 23
    • 33744568633 scopus 로고
    • See the Supporting Information for more details.
    • Takahashi, S.; Kusumi, T.; Kakisawa, H. Chem Lett. 1979,515. See the Supporting Information for more details.
    • (1979) Chem Lett. , vol.515
    • Takahashi, S.1    Kusumi, T.2    Kakisawa, H.3
  • 26
    • 33744628242 scopus 로고    scopus 로고
    • Use of chiral substituents on the boron was indispensable for the observed diastereoselectivity, since use of the isopropyl boronate yielded alcohol 4 with complete scrambling of the stereochemistry at the C12 center, while use of the (D)-DIPT boronate afforded preferentially 4 with the unwanted stereoisomer at C12.
    • Use of chiral substituents on the boron was indispensable for the observed diastereoselectivity, since use of the isopropyl boronate yielded alcohol 4 with complete scrambling of the stereochemistry at the C12 center, while use of the (D)-DIPT boronate afforded preferentially 4 with the unwanted stereoisomer at C12.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.