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Volumn 12, Issue 22, 2010, Pages 5322-5325

Coupling the petasis condensation to an iron(III) chloride-promoted cascade provides a short synthesis of Relenza congeners

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE; DRUG DERIVATIVE; FERRIC CHLORIDE; FERRIC ION; ZANAMIVIR;

EID: 78449278429     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102326b     Document Type: Article
Times cited : (32)

References (34)
  • 5
    • 78449284301 scopus 로고    scopus 로고
    • Recent reviews on Tamiflu synthesis
    • Recent reviews on Tamiflu synthesis
  • 8
    • 70349095283 scopus 로고    scopus 로고
    • Magano, J. Chem. Rev. 2009, 109, 4398-4438
    • (2009) Chem. Rev. , vol.109 , pp. 4398-4438
    • Magano, J.1
  • 14
    • 78449283555 scopus 로고    scopus 로고
    • For a recent use of the Petasis reaction in a de novo synthesis of the sialic acids, see
    • For a recent use of the Petasis reaction in a de novo synthesis of the sialic acids, see
  • 22
    • 78449300085 scopus 로고    scopus 로고
    • This side reaction reveals a poor reactivity of the boronic acid
    • This side reaction reveals a poor reactivity of the boronic acid.
  • 23
    • 78449302507 scopus 로고    scopus 로고
    • With these optimized microwave conditions, the reaction with aminodiphenylmethane, a primary hindered amine that usually performs well in the Petasis reaction, did not afford the desired compound in a satisfying yield
    • With these optimized microwave conditions, the reaction with aminodiphenylmethane, a primary hindered amine that usually performs well in the Petasis reaction, did not afford the desired compound in a satisfying yield.
  • 24
    • 78449288597 scopus 로고    scopus 로고
    • Preservation of the enantiomeric purity was confirmed by chiral HPLC
    • Preservation of the enantiomeric purity was confirmed by chiral HPLC.
  • 29
    • 78449293960 scopus 로고    scopus 로고
    • As a 65:35 mixture of anomer in the favor of the β one, which was confirmed by a NOE effect between H-6 and the hydrogen of the hydroxyl proton at the C2
    • As a 65:35 mixture of anomer in the favor of the β one, which was confirmed by a NOE effect between H-6 and the hydrogen of the hydroxyl proton at the C2.
  • 30
    • 78449268757 scopus 로고    scopus 로고
    • A similar oxazoline is in fact the key intermediate in the synthesis of zanamivir from Neu5Ac. See ref 5
    • A similar oxazoline is in fact the key intermediate in the synthesis of zanamivir from Neu5Ac. See ref 5.
  • 31
    • 78449301297 scopus 로고    scopus 로고
    • 2O and water (4 equiv) under otherwise identical conditions (rt for 24 h) provided a complex reaction mixture from which oxazoline 22a (14%) and a hemiacetal analogous to 18 (13%) could be isolated
    • 2O and water (4 equiv) under otherwise identical conditions (rt for 24 h) provided a complex reaction mixture from which oxazoline 22a (14%) and a hemiacetal analogous to 18 (13%) could be isolated.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.