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Volumn 65, Issue 17, 2000, Pages 5416-5419

Synthesis of cycloheptenols from carbohydrates by ring-closing metathesis

Author keywords

[No Author keywords available]

Indexed keywords

ALICYCLIC HYDROCARBON; CARBOHYDRATE; CYCLOHEPTENE;

EID: 0034714553     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000110o     Document Type: Note
Times cited : (39)

References (66)
  • 42
    • 0033618523 scopus 로고    scopus 로고
    • and for an excellent review on the synthesis of medium-sized rings via free radicals: (m) Yet, L. Tetrahedron 1999, 55, 9349.
    • (1999) Tetrahedron , vol.55 , pp. 9349
    • Yet, L.1
  • 43
    • 0033523035 scopus 로고    scopus 로고
    • For the synthesis of polyfunctionalized cycloheptanes from sugars via 1,3-dipolar nitrone cycloaddition, see: Marco-Contelles, J.; de Opazo, E. Tetrahedron Lett. 1999, 40, 4445.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 4445
    • Marco-Contelles, J.1    De Opazo, E.2
  • 44
    • 0030936007 scopus 로고    scopus 로고
    • The role of the absolute configuration of the stereocenters around the olefinic bonds and the strong effect of the free hydroxyl versus protected O-groups in the RCM reactions have been observed before: (a) Hammer, K.; Undheim, K. Tetrahedron 1997, 53, 5925.
    • (1997) Tetrahedron , vol.53 , pp. 5925
    • Hammer, K.1    Undheim, K.2
  • 51
    • 0343682014 scopus 로고    scopus 로고
    • note
    • The RCM reaction of precursor 2a using methylene chloride at reflux gave the same result [45% (70%) after 7 days]. When toluene was tested as solvent the yield [17% (26%) after 2 days] was worse and extended decomposition was observed.
  • 53
    • 0027218926 scopus 로고
    • The importance of preexisting heterocycles in selected positions and orientations on acyclic precursors for successful carbocyclization processes has been demostrated in our laboratory: (a) Marco-Contelles, J.; Ruiz, P.; Martínez, L.; Martínez-Grau, A. Tetrahedron 1993, 49, 6669.
    • (1993) Tetrahedron , vol.49 , pp. 6669
    • Marco-Contelles, J.1    Ruiz, P.2    Martínez, L.3    Martínez-Grau, A.4
  • 56
    • 0032567372 scopus 로고    scopus 로고
    • [for an application of the results reported in this paper, see: (c) Gómez, A. M.; Danelón, G. O.; Valverde, S.; López, J. C. J. Org. Chem. 1998, 63, 9626; Corrigendum: J. Org. Chem. 1999, 64, 7280].
    • (1999) Corrigendum: J. Org. Chem. , vol.64 , pp. 7280
  • 59
    • 0030857814 scopus 로고    scopus 로고
    • The RCM reactions are very sensitive to steric hindrance close to the double bonds to be metathesized: Fürstner, A., Langemann, K. Synthesis 1997, 792.
    • (1997) Synthesis , pp. 792
    • Fürstner, A.1    Langemann, K.2
  • 64
    • 0342811715 scopus 로고    scopus 로고
    • note
    • See ref 2e for some recent, interesting results, regarding the influence of the absolute stereochemistry of the different hydroxyl protecting groups in sugar templates, on the course of RCM reactions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.