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Volumn 42, Issue 11, 2003, Pages 1258-1262

Total synthesis of phorboxazole A

Author keywords

Antitumor agents; Asymmetric allylation; Macrolides; Natural products; Total synthesis

Indexed keywords

POSITIVE IONS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 0037451442     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390322     Document Type: Article
Times cited : (94)

References (49)
  • 25
    • 0012862872 scopus 로고    scopus 로고
    • c) After submission of this manuscript for publication, we were informed that Prof. G. Pattenden et al. have also completed a synthesis of phorboxazole A. See preceding paper; M. A. Gonzalez, G. Pattenden, Angew. Chem. 2003, 115, 1293; Angew. Chem. Int. Ed. 2003, 42, 1255.
    • (2003) Angew. Chem. , vol.115 , pp. 1293
    • Gonzalez, M.A.1    Pattenden, G.2
  • 26
    • 0038401153 scopus 로고    scopus 로고
    • c) After submission of this manuscript for publication, we were informed that Prof. G. Pattenden et al. have also completed a synthesis of phorboxazole A. See preceding paper; M. A. Gonzalez, G. Pattenden, Angew. Chem. 2003, 115, 1293; Angew. Chem. Int. Ed. 2003, 42, 1255.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1255
  • 28
    • 0034679519 scopus 로고    scopus 로고
    • a) D. A. Evans, V. J. Cee, T. E. Smith, D. M. Fitch, P. S. Cho, Angew. Chem. 2000, 112, 2633; Angew. Chem. Int. Ed. 2000, 39, 2533;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 2533
  • 29
  • 30
    • 0034679493 scopus 로고    scopus 로고
    • b) D. A. Evans, D. M. Fitch, Angew. Chem. 2000, 112, 2636; Angew. Chem. Int. Ed. 2000, 39, 2536.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 2536
  • 31
    • 85007644768 scopus 로고    scopus 로고
    • note
    • The aldehyde 6, which bears the primary pivaloate, was prepared by the same route as previously described for the corresponding MOM ether in 62% overall yield.
  • 32
    • 85007653720 scopus 로고    scopus 로고
    • note
    • Stannane 7 is conveniently prepared by deprotonation of 3-methyl-3-buten-1-ol with two equivalents of Schlosser's base, quenching the resulting dianion with tributyltin iodide, and protection of the resultant alcohol (TBSCI, imidazole).
  • 33
    • 33845183116 scopus 로고
    • E. J. Corey, C. M. Yu, S. S. Kim, J. Am. Chem. Soc. 1989, 111, 5495. For development of this asymmetric allylation methodology, see: D. R. Williams, D. A. Brooks, K. G. Meyer, M. P. Clark, Tetrahedron Lett. 1998, 39, 7251.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 5495
    • Corey, E.J.1    Yu, C.M.2    Kim, S.S.3
  • 34
    • 0032192220 scopus 로고    scopus 로고
    • E. J. Corey, C. M. Yu, S. S. Kim, J. Am. Chem. Soc. 1989, 111, 5495. For development of this asymmetric allylation methodology, see: D. R. Williams, D. A. Brooks, K. G. Meyer, M. P. Clark, Tetrahedron Lett. 1998, 39, 7251.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7251
    • Williams, D.R.1    Brooks, D.A.2    Meyer, K.G.3    Clark, M.P.4
  • 35
    • 85007624890 scopus 로고    scopus 로고
    • note
    • Small-scale reactions permitted the chromatographic separation of homoallylic alcohol diastereomers for individual characterization. Preparative multigram reactions were conveniently carried forward to acetal 16, where the desired C37 isomer was easily purified by flash chromatography.
  • 45
    • 85007624897 scopus 로고    scopus 로고
    • note
    • 13C NMR spectroscopic analysis.
  • 46
    • 85007638185 scopus 로고    scopus 로고
    • note
    • Model studies had shown that individual diastereomericallylic alcoholswere cyclized under these conditions to afford the same tetrahydropyran product.
  • 47
    • 85007643343 scopus 로고    scopus 로고
    • note
    • 3N.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.