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Volumn 4, Issue 19, 2002, Pages 3239-3242

Toward the total synthesis of disorazole A1 and C1: Asymmetric synthesis of a masked southern segment

Author keywords

[No Author keywords available]

Indexed keywords

DISORAZOLE C1; DISORAZPOLE A1; OXAZOLE DERIVATIVE;

EID: 0037136470     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026468j     Document Type: Article
Times cited : (31)

References (37)
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    • Late-stage transformation of alkynes to Z-olefins has been used in a variety of natural product synthesis. For recent examples, see: (a) Wender, P. A.; Hegde, S. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 4956-4957.
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    • (c) Babudri, F.; Fiandanese, V.; Marchese, G.; Punzi, A. Tetrahedron 2000, 56, 327-331. See also [18]annulene: Stöckel, K.; Sondheimer, F. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, pp 68-75.
    • (2000) Tetrahedron , vol.56 , pp. 327-331
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  • 10
    • 23544453285 scopus 로고    scopus 로고
    • Wiley: New York, 1988; Collect.
    • (c) Babudri, F.; Fiandanese, V.; Marchese, G.; Punzi, A. Tetrahedron 2000, 56, 327-331. See also [18]annulene: Stöckel, K.; Sondheimer, F. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, pp 68-75.
    • Organic Syntheses , vol.6 , pp. 68-75
    • Stöckel, K.1    Sondheimer, F.2
  • 13
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    • All minimizations are calculated without a solvent model to complete convergence. Monte Carlo searches are run until the global minimum is found more than once. Goodmann, J. M.; Still, W. C. J. Comput. Chem. 1991, 12, 1110-1117.
    • (1991) J. Comput. Chem. , vol.12 , pp. 1110-1117
    • Goodmann, J.M.1    Still, W.C.2
  • 14
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    • 1 containing a C11′-C12′ alkyne leads preferentially to the 15-membered macrolactone: Hillier, M. C.; Price, A. T.; Meyers, A. I. J. Org. Chem. 2001, 66, 6037-6045.
    • (2001) J. Org. Chem. , vol.66 , pp. 6037-6045
    • Hillier, M.C.1    Price, A.T.2    Meyers, A.I.3
  • 16
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    • The enantiomeric excess is estimated to be higher than 94% by two independent methods (chiral GC, Mosher ester analysis)
    • The enantiomeric excess is estimated to be higher than 94% by two independent methods (chiral GC, Mosher ester analysis).
  • 20
    • 0042318237 scopus 로고    scopus 로고
    • PMB-protected 3-hydroxypropanal 13 is prepared from 1,3-propandiol by mono PMB protection and Parikh-Doering oxidation in 77% overall yield
    • PMB-protected 3-hydroxypropanal 13 is prepared from 1,3-propandiol by mono PMB protection and Parikh-Doering oxidation in 77% overall yield.
  • 24
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    • 3. The measured enantiomeric excess of 88% is in agreement with comparable literature results: Mulzer, J.; Mantoulidis, A.; Öhler, E. J. Org. Chem. 2000, 65, 7456-7467.
    • (2000) J. Org. Chem. , vol.65 , pp. 7456-7467
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    • As in similar cases with sterically very demanding ketones, the Me-CBS reagent has to be used in excess: Trost, B. M.; Gunzner, J. L. J. Am. Chem. Soc. 2001, 123, 9449-9450.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9449-9450
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    • (1998) Metal-Catalyzed Cross-Coupling Reactions , pp. 203-229
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.