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Volumn 5, Issue 1, 2003, Pages 35-38

1,6-Asymmetric induction in boron-mediated aldol reactions: Application to a practical total synthesis of (+)-discodermolide

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ANTINEOPLASTIC AGENT; BORON DERIVATIVE; DISCODERMOLIDE; ALKANE; BORON; CARBAMIC ACID DERIVATIVE; LACTONE; PYRONE DERIVATIVE;

EID: 0037900065     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0270780     Document Type: Article
Times cited : (88)

References (34)
  • 2
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    • Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Schulte, G. K. J. Org. Chem. 1990, 55, 4912. Additions and corrections: J. Org. Chem. 1991, 56, 1346.
    • (1991) J. Org. Chem. , vol.56 , pp. 1346
  • 5
    • 0035416117 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Altmann, K. H. Curr. Opin. Chem. Biol. 2001, 5, 424. (b) He, L. F.; Orr, G. A.; Horwitz, S. B. Drug Discovery Today 2001, 6, 1153. (c) Stachel, S. J.; Biswas, K.; Danishefsky, S. J. Curr. Pharm. Design 2001, 7, 1277.
    • (2001) Curr. Opin. Chem. Biol. , vol.5 , pp. 424
    • Altmann, K.H.1
  • 6
    • 0035889710 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Altmann, K. H. Curr. Opin. Chem. Biol. 2001, 5, 424. (b) He, L. F.; Orr, G. A.; Horwitz, S. B. Drug Discovery Today 2001, 6, 1153. (c) Stachel, S. J.; Biswas, K.; Danishefsky, S. J. Curr. Pharm. Design 2001, 7, 1277.
    • (2001) Drug Discovery Today , vol.6 , pp. 1153
    • He, L.F.1    Orr, G.A.2    Horwitz, S.B.3
  • 7
    • 0034857182 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Altmann, K. H. Curr. Opin. Chem. Biol. 2001, 5, 424. (b) He, L. F.; Orr, G. A.; Horwitz, S. B. Drug Discovery Today 2001, 6, 1153. (c) Stachel, S. J.; Biswas, K.; Danishefsky, S. J. Curr. Pharm. Design 2001, 7, 1277.
    • (2001) Curr. Pharm. Design , vol.7 , pp. 1277
    • Stachel, S.J.1    Biswas, K.2    Danishefsky, S.J.3
  • 14
    • 0141583121 scopus 로고    scopus 로고
    • Ph.D. Thesis, Harvard University, Cambridge
    • (h) Halstead, D. P. Ph.D. Thesis, Harvard University, Cambridge, 1998.
    • (1998)
    • Halstead, D.P.1
  • 31
    • 0141694744 scopus 로고    scopus 로고
    • note
    • To achieve an efficient alkylation with iodide 18, incorporation of an electron-donating 4-methoxy group into the aryl acetate was required. The subsequent aldol coupling of 5 with 6 and ester reduction steps proceeded in comparable yield to that obtained previously for the corresponding Heathcock aryl ester (ref 6a).
  • 34
    • 0141583083 scopus 로고    scopus 로고
    • note
    • To date, we have performed this key aldol coupling on a gram scale. In contrast, by using the lithium enolate from 3, the addition proceeds under Felkin-Anh induction from the aldehyde 2 and leads to exclusively the undesired (SR) configuration.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.