메뉴 건너뛰기




Volumn 10, Issue 21, 2008, Pages 4747-4750

A concise approach to a gelsemine core structure using an oxygen to carbon bridge swapping strategy

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CARBON; GELSEMINE; OXYGEN; UNCLASSIFIED DRUG;

EID: 58149163163     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801835q     Document Type: Article
Times cited : (15)

References (26)
  • 2
    • 46149125082 scopus 로고    scopus 로고
    • Lovell, F. M.; Pepinsky, R.; Wilson, A. J. C Tetrahedron Lett. 1959, 1, 1-5.
    • Lovell, F. M.; Pepinsky, R.; Wilson, A. J. C Tetrahedron Lett. 1959, 1, 1-5.
  • 16
    • 84918067441 scopus 로고    scopus 로고
    • Only a few examples of malonate additions to benzocycloheptadienone dicarboxylate were reported by Fohlisch's group: Föhlisch, B, Schupp, E, Dukek, U, Graessle, I. Liebigs Ann. Chem. 1973, 1851
    • Only a few examples of malonate additions to benzocycloheptadienone dicarboxylate were reported by Fohlisch's group: Föhlisch, B.; Schupp, E.; Dukek, U.; Graessle, I. Liebigs Ann. Chem. 1973, 1851.
  • 20
    • 60949097608 scopus 로고    scopus 로고
    • Temporary TBS protection was required to avoid major loss of material due to the high water solubility of the deprotected form of 8
    • Temporary TBS protection was required to avoid major loss of material due to the high water solubility of the deprotected form of 8.
  • 24
    • 60949100987 scopus 로고    scopus 로고
    • No reaction was observed at 80 °C.
    • No reaction was observed at 80 °C.
  • 25
    • 60949104495 scopus 로고    scopus 로고
    • Most of the bicyclic adducts existed as mixtures of two epimers due to the easily epimerizable center α to the nitrile, but this was of no consequence for later chemistry. Tricycles 12 and 14 were single isomers, as shown in Figure 1 for 12
    • Most of the bicyclic adducts existed as mixtures of two epimers due to the easily epimerizable center α to the nitrile, but this was of no consequence for later chemistry. Tricycles 12 and 14 were single isomers, as shown in Figure 1 for 12.
  • 26
    • 60949090087 scopus 로고    scopus 로고
    • The epimerization of 2 with Et3N is puzzling, bearing in mind that 2 is obtained from 14 as a single epimer from much more strongly basic conditions. We have no convincing rationale for this result but consider it possible that under the conditions used in Scheme 6 the configuration of the ester could be temporarily locked by formation of a lactone acetal (i, which is then opened by MeOH on work-up addition of solid NB 4Cl, Equation Presented
    • 4Cl). (Equation Presented)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.