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Volumn 46, Issue 45, 2005, Pages 7793-7796

Synthesis of the floresolide B hydroquinone lactone core using ring-closing metathesis

Author keywords

Floresolide; Ring closing metathesis; Synthesis

Indexed keywords

CYCLOPHANE DERIVATIVE; FLORESOLIDE B; HYDROQUINONE DERIVATIVE; LACTONE DERIVATIVE; LEWIS ACID; UNCLASSIFIED DRUG;

EID: 26444620727     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.023     Document Type: Article
Times cited : (20)

References (53)
  • 9
    • 13244289910 scopus 로고    scopus 로고
    • Recent reviews that include ring-closing metathesis: D. Astruc New J. Chem. 29 2005 42 56
    • (2005) New J. Chem. , vol.29 , pp. 42-56
    • Astruc, D.1
  • 19
    • 20544456651 scopus 로고    scopus 로고
    • For a related discussion and leading references, see: H. Yanai, A. Saito, and T. Taguchi Tetrahedron 61 2005 7087 7093
    • (2005) Tetrahedron , vol.61 , pp. 7087-7093
    • Yanai, H.1    Saito, A.2    Taguchi, T.3
  • 25
    • 26444533980 scopus 로고    scopus 로고
    • Related examples in a six-membered ring: Ref. 7a,7c and 7d.
    • 7d.
  • 35
    • 0035914011 scopus 로고    scopus 로고
    • 7c and C.W. Lee, and R.H. Grubbs J. Org. Chem. 66 2001 7155 7158 This latter report includes a seven-membered lactone that could not be formed by RCM
    • (2001) J. Org. Chem. , vol.66 , pp. 7155-7158
    • Lee, C.W.1    Grubbs, R.H.2
  • 40
    • 0000217402 scopus 로고
    • Claisen Rearrangements
    • B.M. Trost I. Fleming Pergamon Press Elmsford, NY
    • P. Wipf Claisen Rearrangements B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Press Elmsford, NY 827 873
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 827-873
    • Wipf, P.1
  • 44
    • 26444600756 scopus 로고    scopus 로고
    • note
    • We refer to 11 as a 'pseudo-dimer' of 8 because one mole of 11 comprises two moles of 8 minus one mole of ethylene.
  • 45
    • 0043194171 scopus 로고    scopus 로고
    • For a general discussion of the formation of dimeric-type cross-metathesis intermediates en route to secondary metathesis products, see: A.K. Chatterjee, T.-L. Choi, D.P. Sanders, and R.H. Grubbs J. Am. Chem. Soc. 125 2003 11360 11370
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 11360-11370
    • Chatterjee, A.K.1    Choi, T.-L.2    Sanders, D.P.3    Grubbs, R.H.4
  • 46
    • 26444531903 scopus 로고    scopus 로고
    • note
    • Upon increasing the concentration to 0.1 mol/L the ring-closing metathesis was largely shut down. A range of products stemming from alkene migration and cross-metathesis formed, but the isopropenyl group was unaffected.
  • 49
    • 26444577785 scopus 로고    scopus 로고
    • note
    • See Supporting Information for a reasonable reaction pathway leading from lactone 12 to naphthol 13.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.