메뉴 건너뛰기




Volumn , Issue 9, 2007, Pages 939-941

Formal synthesis of (+)-SCH 351448: The Prins cyclization approach

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; BROMIDE; LOW DENSITY LIPOPROTEIN RECEPTOR; MONOMER; NATURAL PRODUCT; SCH 351448; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33847144939     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b616558c     Document Type: Article
Times cited : (59)

References (35)
  • 7
    • 33746119978 scopus 로고    scopus 로고
    • For selected literature on the Prins cyclization, see
    • M. T. Crimmins S. Grace Org. Lett. 2006 8 2887
    • (2006) Org. Lett. , vol.8 , pp. 2887
    • Crimmins, M.T.1    Grace, S.2
  • 22
    • 33845374534 scopus 로고
    • Other allylation methods used resulted in lower yields and enantiomeric excess of the homoallylic alcohol 6. For references on the allylation methods, see
    • H. C. Brown P. K. Jadhav K. S. Bhat T. Perumal J. Org. Chem. 1986 51 432
    • (1986) J. Org. Chem. , vol.51 , pp. 432
    • Brown, H.C.1    Jadhav, P.K.2    Bhat, K.S.3    Perumal, T.4
  • 32
    • 33847099760 scopus 로고    scopus 로고
    • 16 of 2 via a radical mechanism resulted in an incomplete conversion to unconjugated aldehyde 2a. The failure to separate the 2 and 2a rendered spectroscopic analysis very difficult
    • 16 of 2 via a radical mechanism resulted in an incomplete conversion to unconjugated aldehyde 2a. The failure to separate the 2 and 2a rendered spectroscopic analysis very difficult
  • 33
    • 33847170711 scopus 로고    scopus 로고
    • A significant amount of unreacted homoallylic alcohol 3 was recovered in the three entries (6 to 8) in Table 1. There are possibly other competing reactions which degrade this reactive aldehyde 2a in the presence of a Lewis acid before Prins cyclization can take place
    • A significant amount of unreacted homoallylic alcohol 3 was recovered in the three entries (6 to 8) in Table 1. There are possibly other competing reactions which degrade this reactive aldehyde 2a in the presence of a Lewis acid before Prins cyclization can take place
  • 34
    • 33847174742 scopus 로고    scopus 로고
    • ACCN denotes 1,1′-azobis(cyclohexane) carbonitrile, a synthetic equivalent to AIBN
    • ACCN denotes 1,1′-azobis(cyclohexane) carbonitrile, a synthetic equivalent to AIBN


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.