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Volumn 45, Issue 33, 2006, Pages 5506-5510

Toward the total synthesis of spirastrellolide A. Part 1: Strategic considerations and preparation of the southern domain

Author keywords

Antitumor agents; Macrolides; Natural products; Phosphatase inhibitors; Total synthesis

Indexed keywords

ANTITUMOR AGENTS; MACROLIDES; NATURAL PRODUCTS; PHOSPHATASE INHIBITORS; TOTAL SYNTHESIS;

EID: 33748661293     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601654     Document Type: Article
Times cited : (70)

References (49)
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    • Recent reviews on phosphatases as targets for medicinal chemistry: a) L. Bialy, H. Waldmann, Angew. Chem. 2005, 117, 3880-3906;
    • (2005) Angew. Chem. , vol.117 , pp. 3880-3906
    • Bialy, L.1    Waldmann, H.2
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    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 3814-3839
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    • Angew. Chem. Int. Ed. 2000, 39, 3012-3043.
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    • Angew. Chem. Int. Ed. 2006, 45, 5510-5515.
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 5510-5515
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    • note
    • Note that a late-stage fragment coupling between the northern and the southern domain at C25/C26 by metathesis (or other suitable olefination reactions) is envisaged (cf. Scheme 2); a selective hydrogenation of this newly formed alkene in the presence of a pre-existing Z olefin at C15/C16 might raise serious selectivity issues.
  • 37
    • 0000172128 scopus 로고    scopus 로고
    • (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin
    • Review: T. Ohkuma, R. Noyori in Comprehensive Asymmetric Catalysis, Vol. 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 199-246.
    • (1999) Comprehensive Asymmetric Catalysis, Vol. 1 , vol.1 , pp. 199-246
    • Ohkuma, T.1    Noyori, R.2
  • 40
    • 0041733422 scopus 로고    scopus 로고
    • For pertinent examples of 1,5-anti stereoinduction in boron aldol chemistry as required in the present case, see: a) D. A. Evans, B. Côté, P. J. Coleman, B. T. Connell, J. Am. Chem. Soc. 2003, 125, 10 893-10 898;
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 10893-10898
    • Evans, D.A.1    Côté, B.2    Coleman, P.J.3    Connell, B.T.4
  • 46
    • 33748642911 scopus 로고    scopus 로고
    • note
    • A series of control experiments and detailed analyses of the Mosher esters confirmed the proposed stereochemical assignments; details will be reported in a forthcoming report.
  • 49
    • 33748665354 scopus 로고    scopus 로고
    • see the Supporting Information
    • Comparison of the NMR data of the individual isomers (see the Supporting Information) with the reported data of 1, however, do not allow us to decide which relative configuration is present in the natural product.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.