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Volumn 125, Issue 43, 2003, Pages 13132-13142

Structure Assignment, Total Synthesis, and Antiviral Evaluation of Cycloviracin B1

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; DRUG PRODUCTS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 0142214614     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036521e     Document Type: Article
Times cited : (95)

References (118)
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    • note
    • This applies to all 13 individual fattiviracins known to date, cf. refs 2 and 5.
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    • (a) For recent studies on the synthesis of macrodiolides by nontemplated cyclodimerization reactions, see the following leading references and a comprehensive compilation of pertinent literature: Su, Q.; Beeler, A. B.; Lobkovsky, E.; Porco, J. A., Jr.; Panek, J. S. Org. Lett. 2003, 5, 2149.
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    • (b) For the synthesis of a natural product from our laboratory by an RCM-based cyclodimerization process, see: Fürstner, A.; Thiel, O. R.; Ackermann, L. Org. Lett. 2001, 3, 449.
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    • Fürstner, A.1    Thiel, O.R.2    Ackermann, L.3
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    • Only very few examples of ring-opening Claisen condensations are known using four- to six-membered lactones as the substrates, cf: (a) Bone, E. A.; Davidson, A. H.; Lewis, C. N.; Todd, R. S. J. Med. Chem. 1992, 35, 3388.
    • (1992) J. Med. Chem. , vol.35 , pp. 3388
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    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin
    • (b) Ohkuma, T.; Noyori, R. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 1; pp 199-246.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1 , pp. 199-246
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    • note
    • The order of silylation and hydrogenation can also be inversed. In this case, however, the overall yield of product 6 is somewhat lower due to partial cleavage of the terminal TBDPS group during the asymmetric reduction step.
  • 45
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    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • (b) Schmidt, R. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6; pp 33-61.
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    • note
    • The synthesis of this compound is outlined in the Supporting Information.
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    • Jpn. Kokai Tokkyo Koho Jpn. Pat. 11246587 (1999-09-14)
    • (a) Hyoda, T.; Tsuchira, Y.; Sekine, A.; Amano, T. Jpn. Kokai Tokkyo Koho Jpn. Pat. 11246587 (1999-09-14).
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    • For methods allowing the determination of the configuration of secondary alcohols by using sugar derivatives as derivatizing agents, see the following for leading references and literature cited therein: (a) Trujillo, M.; Morales, E. Q.; Vazquez, J. T. J. Org. Chem. 1994, 59, 6637.
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  • 67
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    • Enantiopure propene oxide is commercially available or can be conveniently prepared on a large scale in optically active form using Jacobsens's excellent HKR method, cf.: (a) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936.
    • (1997) Science , vol.277 , pp. 936
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    • note
    • 1H NMR spectra which are also distinctly different for the pairs of stereoisomers 31/33, 42/43, 44/45. Particularly diagnostic is the shift of the terminal methyl group of the fatty acid chain which resonates at Δ = 1.34 ppm in the 17S-configured compounds but at Δ = 1.31 ppm in the 17R-configured products. The pertinent shift in the natural product is Δ = 1.34 ppm.
  • 75
    • 0142243655 scopus 로고    scopus 로고
    • note
    • If the fatty acids are drawn in a zigzag conformation, all hydroxyl groups are located on the same side; the fact that the centers at C-17' and C-19 are S-configured while the other ones are R-configured simply reflects the formalism of the Cahn - Ingold-Prelog nomenclature.
  • 79
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    • note
    • Note again the formalism of the Chan-Ingold-Prelog nomenclature. The use of the (2R)-configured aldehyde 58 will ultimately result in a (19S)-configured cycloviracin derivative due to change in priorities of the substituents at that center.
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    • See the following for leading references on the applications of Julia-Kocienski olefination reactions to the total synthesis of complex targets: (a) Kang, S. H.; Jeong, J. W.; Hwang, Y. S.; Lee, S. B. Angew. Chem., Int. Ed. 2002, 41, 1392.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1392
    • Kang, S.H.1    Jeong, J.W.2    Hwang, Y.S.3    Lee, S.B.4
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    • refs 18a and 38c
    • See the following for general reviews on diorganozinc addition reactions to aldehydes: (a) refs 18a and 38c.
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    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer, Berlin
    • (c) Soai, K.; Shibata, T. In Comprehensive Asymmetric Catalysis, Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer, Berlin, 1999; Vol. 2; pp 911-922.
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 911-922
    • Soai, K.1    Shibata, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.