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Volumn 45, Issue 22, 2006, Pages 3651-3653

Total synthesis of (+)-machaeriol D with a key regio- and stereoselective S N2′ reaction

Author keywords

Allylic substitution; Asymmetric synthesis; Benzopyrans; Cyanocuprate reagents; Natural products

Indexed keywords

ALLYLIC SUBSTITUTION; ASYMMETRIC SYNTHESIS; BENZOPYRANS; CYANOCUPRATE REAGENTS; NATURAL PRODUCTS;

EID: 33746299533     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600006     Document Type: Article
Times cited : (49)

References (52)
  • 25
    • 33845183760 scopus 로고
    • N2′ reactions, see: a) J. A. Marshall, Chem. Rev. 1989, 89, 1503;
    • (1989) Chem. Rev. , vol.89 , pp. 1503
    • Marshall, J.A.1
  • 50
    • 33746275573 scopus 로고    scopus 로고
    • note
    • The freshly prepared aryl magnesium bromide was added to an equivalent amount of reagent-grade cuprous cyanide (Aldrich) in anhydrous THF at -40°C under a nitrogen atmosphere. The initially suspended cuprous cyanide went into solution within 1 h upon warming from -40 to 0°C.
  • 51
    • 33746306168 scopus 로고    scopus 로고
    • note
    • Back-transformation of 3 to 11 in the presence of acid was the reason for the failure of these reactions.
  • 52
    • 33746294682 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy (400 MHz).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.