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Volumn 127, Issue 12, 2005, Pages 4297-4307

Total syntheses of amphidinolides T1 and T4 via catalytic, stereoselective, reductive macrocyclizations

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSIS; NICKEL; REDUCTION; STEREOCHEMISTRY;

EID: 16244420717     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja042733f     Document Type: Article
Times cited : (93)

References (75)
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    • For the isolation, structure determination, and biological studies of Amphidinolides T1-5, see: (a) Tsuda, M.; Endo, T.; Kobayashi, J. J. Org. Chem. 2000, 65, 1349-1352.
    • (2000) J. Org. Chem. , vol.65 , pp. 1349-1352
    • Tsuda, M.1    Endo, T.2    Kobayashi, J.3
  • 26
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    • Several other nickel-catalyzed carbon-carbon bond-forming reactions of alkynes have been developed by Montgomery: (a) Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890-3908.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3890-3908
    • Montgomery, J.1
  • 39
    • 0037148128 scopus 로고    scopus 로고
    • Lewis acid-mediated addition of propargyl nucleophiles to 2-acetoxy tetrahydrofurans is precedented. For the use of propargylmagnesium bromide, see: (a) Franck, X.; Hocquemiller, R.; Figadère, B. Chem. Commun. 2002, 160-161.
    • (2002) Chem. Commun. , pp. 160-161
    • Franck, X.1    Hocquemiller, R.2    Figadère, B.3
  • 44
    • 16244380268 scopus 로고    scopus 로고
    • note
    • This sequence of functional group manipulations was performed as reported in ref 12.
  • 46
    • 33845470817 scopus 로고
    • Allylstannanes are reported to be much more nucleophilic compared to corresponding allylsilanes: (a) Denmark, S. E.; Weber, E. J. J. Am. Chem. Soc. 1984, 106, 7970-7971.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 7970-7971
    • Denmark, S.E.1    Weber, E.J.2
  • 49
    • 0001239629 scopus 로고
    • Allenylstannanes have also been shown to add to thioacetals under Lewis acidic conditions: (d) Sato, T.; Okura, S.; Otera, J.; Nozaki, H. Tetrahedron Lett. 1987, 28, 6299-6302.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 6299-6302
    • Sato, T.1    Okura, S.2    Otera, J.3    Nozaki, H.4
  • 54
    • 16244394914 scopus 로고    scopus 로고
    • note
    • Determined by Mosher ester analysis and ultimate conversion to 1.
  • 55
    • 16244370781 scopus 로고    scopus 로고
    • note
    • Remaining material appeared to be a number of decomposition products of the alkynal that could not be identified.
  • 66
    • 16244375631 scopus 로고    scopus 로고
    • Unpublished results
    • Work in our laboratory has shown that this system is effective for the methylenation of sterically hindered ketones. Jeso, V.; Jamison, T. F. Unpublished results.
    • Jeso, V.1    Jamison, T.F.2
  • 67
    • 16244423062 scopus 로고    scopus 로고
    • note
    • Many alkyne-aldehyde couplings may be conducted in acetone without a decrease in yield. Nevertheless, a notable exception exists, that being an intramolecular, Ni-catalyzed alkyne-ketone coupling observed during studies directed toward the synthesis of terpestacin, ref 22.
  • 68
    • 16244412994 scopus 로고    scopus 로고
    • note
    • Ozonolysis was followed by exposure to dimethyl sulfide affording 9b and another product, determined to be the ozonide at terminal position. Treatment of the ozonide with triphenylphosphine promoted clean conversion to 9b, giving an 80% combined yield of 9b. Direct reductive workup with triphenylphosphine resulted in much lower yields. See Supporting Information for more detail.
  • 69
    • 16244416935 scopus 로고    scopus 로고
    • note
    • 4c NMDPP emerged as a uniquely powerful promoter of asymmetric Ni-catalyzed coupling reactions.
  • 72
    • 16244417862 scopus 로고    scopus 로고
    • note
    • This approach is likely an oversimplification, as it ignores the effects of other stereogenic centers, e.g. those in the tether linking the alkyne and the aldehyde. Related experiments with other sets of diastereomers would directly test these influences and possibly result in further refinement (or revision) of the model proposed herein.
  • 75
    • 0000784039 scopus 로고
    • For an in-depth study of situations in which developing 1,3-interactions (syn-pentane-like) better account for the observed sense of stereoinduction in additions to chiral aldehydes than the Felkin-Anh model; see: Roush, W. R. J. Org. Chem. 1991, 56, 4151-4157.
    • (1991) J. Org. Chem. , vol.56 , pp. 4151-4157
    • Roush, W.R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.