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Volumn 63, Issue 38, 2007, Pages 9373-9381

Effects of α-alkoxy substitution and conformational constraints on 6-exo radical cyclizations of hydrazones via reversible thiyl and stannyl additions

Author keywords

Aminosugars; Dysiherbaine; Radical cyclization; Stereoselectivity

Indexed keywords

AMINOALCOHOL; CARBON; DYSIHERBAINE; FUNCTIONAL GROUP; HYDRAZONE DERIVATIVE; NITROGEN; OXYGEN; TIN DERIVATIVE;

EID: 34547593344     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.06.117     Document Type: Article
Times cited : (14)

References (49)
  • 2
    • 34547575814 scopus 로고    scopus 로고
    • Reviews:
  • 5
    • 0003891487 scopus 로고    scopus 로고
    • Chapleur Y. (Ed), Wiley-VCH, Weinheim
    • In: Chapleur Y. (Ed). Carbohydrate Mimics (1998), Wiley-VCH, Weinheim
    • (1998) Carbohydrate Mimics
  • 10
    • 34547569341 scopus 로고    scopus 로고
    • For studies of activity of (-)-dysiherbaine, see:
  • 34
    • 34547599351 scopus 로고    scopus 로고
    • Reviews of radical addition to C{double bond, long}N bonds:
  • 41
    • 34547575500 scopus 로고    scopus 로고
    • note
    • A mixture of 5- and 6-membered acetals was present, from which the desired regioisomer was obtained in 27% yield after recrystallization.
  • 43
    • 34547578615 scopus 로고    scopus 로고
    • note
    • On larger scale, the arabitol route was preferred due to the cumbersome purification of the 4,6-O-benzylidene-d-galactopyranose.
  • 45
    • 34547569941 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of the crude reaction mixture was consistent with O-acylation. However, 30% recovery of 8 was observed after chromatography.
  • 46
    • 34547605899 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum consistent with 4:1 mixture of diastereomeric diols.
  • 47
    • 34547606779 scopus 로고    scopus 로고
    • note
    • Attempts to form the cyclic carbamate from 21 for NOE analysis were unsuccessful.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.