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Volumn 71, Issue 22, 2006, Pages 8552-8558

Streamlined, asymmetric synthesis of 8,4′-oxyneolignans

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; ESTERS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 33750441173     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061521t     Document Type: Article
Times cited : (41)

References (50)
  • 10
    • 0037034009 scopus 로고    scopus 로고
    • (a) Ridley, R. G. Nature 2002, 415, 686-693.
    • (2002) Nature , vol.415 , pp. 686-693
    • Ridley, R.G.1
  • 22
    • 33750453226 scopus 로고    scopus 로고
    • note
    • In effect, most of the in vitro and in vivo biological evaluations reported so far were effected on racemic mixtures.
  • 33
    • 33750460789 scopus 로고    scopus 로고
    • note
    • Evidence of the full preservation of the enantiopurity of compound 6 was given by optical activity data which were comparable to those reported in the literature (see experimental section in the Supporting Information).
  • 37
    • 0004201576 scopus 로고    scopus 로고
    • Tetrahedron Organic Chemistry Series Pergamon Press: Elsevier: Oxford
    • (c) Gawley, R. E.; Aubé, J. Principles of Asymmetric Synthesis; Tetrahedron Organic Chemistry Series, Vol. 14; Pergamon Press: Elsevier: Oxford, 1996; pp 121-160.
    • (1996) Principles of Asymmetric Synthesis , vol.14 , pp. 121-160
    • Gawley, R.E.1    Aubé, J.2
  • 41
    • 33750444441 scopus 로고    scopus 로고
    • note
    • It is worth noting that the acetyl protection in 11 was critical since installation of electron-donating groups at C-7 hydroxyl causes 11 to collapse into stable epoxide derivatives.
  • 43
    • 33750493140 scopus 로고    scopus 로고
    • note
    • The experimental conditions capitalized on the findings previously reported by Helm and Li (excess cesium 2-methoxyphenolate, 18-crown-6, benzene, reflux, 24 h; ref 14d).
  • 44
    • 33750430479 scopus 로고    scopus 로고
    • note
    • On the basis of our results, the absolute configuration of levorotatory virolin in ref 15a should be reverted (7R,8R).
  • 46
    • 33750445450 scopus 로고    scopus 로고
    • note
    • 3, 18-crown-6 in DMF, sonication) as compared to the previous microwave-assisted substitution procedure (see text) since it is known that the presence of a carboxylate or a carbonyl group adjacent to the alcohol (or bromine) function strongly activates the substrate for nucleophilic displacement. See, for example, ref 16a.
  • 49
    • 33750433404 scopus 로고    scopus 로고
    • note
    • Overall, these findings indirectly confirmed a (7R,8R)-configuration for the minor syn-configured products, whose structures coincide with those of compounds (-)-1, (-)-2, and (-)-3.
  • 50
    • 33750429463 scopus 로고    scopus 로고
    • note
    • 13C chemical shift assignments follow the conventional 8,4′-oxyneolignan numbering. See ref 2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.