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Volumn 68, Issue 21, 2003, Pages 7967-7978

Regulated-stereoselective construction of thirteen stereogenic centers necessary for the frame of (+)-discodermolide, based on iterative Lewis acid-promoted aldol reactions

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; MAGNESIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 0142121846     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034901c     Document Type: Article
Times cited : (39)

References (69)
  • 42
    • 0035812422 scopus 로고    scopus 로고
    • A similar approach with selenides has been reported but it was limited to the α-methyl-β-protected-oxy aldehydes, not bearing the other substituent at the β position, which is essential for a model of aldehydes toward the construction of polypropionate frameworks: (a) Guindon, Y.; Houde, K.; Prévost, M.; Cardinal-David, B.; Landry, S. R.; Daoust, B.; Bencheqroun, M.; Guérin, B. J. Am. Chem. Soc. 2001, 123, 8496-8501.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 8496-8501
    • Guindon, Y.1    Houde, K.2    Prévost, M.3    Cardinal-David, B.4    Landry, S.R.5    Daoust, B.6    Bencheqroun, M.7    Guérin, B.8
  • 48
    • 0142057556 scopus 로고    scopus 로고
    • note
    • -Methyl-1,3-propanediol was purchased from Aldrich.
  • 49
    • 0142089304 scopus 로고    scopus 로고
    • note
    • The silylketene acetal 4 (Z:E = 3:1), which accompanies the corresponding C-silyl ester, by trapping the lithium enolate with TMSOTf.
  • 59
    • 0035829005 scopus 로고    scopus 로고
    • A complete selection in the radical debromination of a series of δ-valerolactones, like 14, was observed to lead an unexpected route to acyclic skeltons: Kiyooka, S.-i.; Li, Y.-N.; Shahid, K. A.; Okazaki, M.; Shuto, Y. Tetrahedron Lett. 2001, 42, 7299-7301.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 7299-7301
    • Kiyooka, S.-I.1    Li, Y.-N.2    Shahid, K.A.3    Okazaki, M.4    Shuto, Y.5
  • 62
    • 19044376917 scopus 로고    scopus 로고
    • In a more simple system, the diastereoselective synthesis of 2,3-anti-3,4-anti and 2,3-anti-3,4-syn propionates has recently been reported by using a tandem sequence of Mukaiyama aldol reaction of α-methyl-β -protected-oxypropanal with a selenoenoxysilane and the following hydrogen transfer reaction: Guindon, Y.; Prévost, M.; Mochirian, P.; Guérin, B. Org. Lett. 2002, 4, 1019-1022.
    • (2002) Org. Lett. , vol.4 , pp. 1019-1022
    • Guindon, Y.1    Prévost, M.2    Mochirian, P.3    Guérin, B.4
  • 64
    • 0142120857 scopus 로고    scopus 로고
    • note
    • In the boron-mediated aldol reactions of similar γ-chiral (Z)-enals, competition between reagent control and substrate control has been observed (ref 3j).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.