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Volumn 7, Issue 19, 2005, Pages 4083-4086

Synthesis of (-)-amphidinolide K fragment C9-C22

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIDINOLIDE K; MACROLIDE;

EID: 25444476745     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051200o     Document Type: Article
Times cited : (54)

References (40)
  • 8
    • 25444529160 scopus 로고    scopus 로고
    • note
    • On the other hand, opening of the lactone ring of 7 with (R,R)-pseudoephedrine and protection/activation of the vicinal diol as a sulfite ester, followed by reaction with 3-methylbutanal (as a model) and tetrahydrofuran ring formation with NaH posed diverse problems, such as a moderate yield of the aldol reaction and no cyclization in the last step. Use of a stronger EWG-sulfate instead of sulfite-posed problems also, i.e., poor yields of the sulfate preparation and a premature elimination reaction.
  • 12
    • 0026739942 scopus 로고
    • Compound (S)-7 is usually obtained through diazotization of L-glutamic acid, lactonization, and reduction of the carboxyl group with borane (or related procedures). See: (a) Lehmann, J.; Pieper, B. Tetrahedron: Asymmetry 1992, 3, 1537.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 1537
    • Lehmann, J.1    Pieper, B.2
  • 16
    • 0001657421 scopus 로고
    • Conversion of 6 to the corresponding epoxyalcohol with titanium tetraisopropoxide and polymethylhydrosiloxane (Reding, M. T.; Buchwald, S. L. J. Org. Chem. 1995, 60, 7884) was not useful as the 4,5-epoxy-1-pentanol isomerized to 5-hydroxymethyloxolane (THF derivative) under the reaction conditions, as might be expected.
    • (1995) J. Org. Chem. , vol.60 , pp. 7884
    • Reding, M.T.1    Buchwald, S.L.2
  • 20
    • 25444518891 scopus 로고    scopus 로고
    • note
    • 4, and finally 1.1 equiv of DIPEA.
  • 21
    • 25444471492 scopus 로고    scopus 로고
    • PhD Thesis, Universitat de Barcelona
    • iPr) afforded a mixture of two aldols: Mas, G. PhD Thesis, Universitat de Barcelona, 2000.
    • (2000)
    • Mas, G.1
  • 22
    • 25444438951 scopus 로고    scopus 로고
    • Master's Thesis, Universitat de Barcelona
    • (c) When parallel aldol-like reactions were carried out in our lab with thiazolidine-2-thione chiral auxiliaries (instead of the oxazolidin-2-one derivatives shown in Schemes 2 and 4), the results were disappointing: Batlle, M. Master's Thesis, Universitat de Barcelona, 2003.
    • (2003)
    • Batlle, M.1
  • 25
  • 30
    • 25444504467 scopus 로고    scopus 로고
    • note
    • For the cleavage of the final boron complexes, in all cases the reaction mixtures were quenched at low temperature with MeOH and buffered water (pH 7). The resulting solutions or suspensions were stirred for ca. 12 h (no hydrogen peroxide or bases were added).
  • 33
    • 25444531643 scopus 로고    scopus 로고
    • note
    • 3H ("Superhydride", 2.2 equiv) in THF at -78°C cleaved exclusively the chiral auxiliary of 11; however, in the case of 23, several products were produced.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.