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Volumn 45, Issue 10, 2004, Pages 2053-2056

A new synthesis of key intermediates for the assembly of polycyclic ethers: Yb(OTf)3-promoted formation of O,S-acetals from α- fluorosulfides and alcohols

Author keywords

Ciguatoxin; Convergent synthesis; Nucleophilic addition; O,S Acetal; Polyether; Fluorosulfide

Indexed keywords

ACETAL DERIVATIVE; ALCOHOL DERIVATIVE; ETHER DERIVATIVE; FLUORINE DERIVATIVE; SULFIDE; YTTERBIUM;

EID: 1242318517     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.077     Document Type: Article
Times cited : (16)

References (37)
  • 3
  • 23
    • 0344006321 scopus 로고    scopus 로고
    • For recent reviews of RCM, see:
    • For recent reviews of RCM, see: Fürstner A. Angew. Chem., Int. Ed. 39:2000;3013.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3013
    • Fürstner, A.1
  • 31
    • 85030898135 scopus 로고    scopus 로고
    • For recent reviews on glycosyl fluorides, see
    • For recent reviews on glycosyl fluorides, see Shimizu M., Togo H., Yokoyama M. Synthesis. 1998;800.
    • (1998) Synthesis , pp. 800
    • Shimizu, M.1    Togo, H.2    Yokoyama, M.3
  • 33
    • 85030893946 scopus 로고    scopus 로고
    • note
    • The important aspect of the mixed-acetal strategy is that the stereoselective synthesis of the O,S-acetal is not necessary, because the stereochemical information at the acetal carbon is lost upon radical cyclization conditions ( 8 → 9 ). See Refs. 8 and 9.
  • 34
    • 85030893958 scopus 로고    scopus 로고
    • note
    • 3N] to give α-fluorosulfide 21 (48 mg) in 100% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.