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Volumn 61, Issue 13, 1996, Pages 4427-4433

Complete diastereocontrol in intramolecular 1,3-dipolar cycloadditions of 2-substituted 5-hexenyl and 5-heptenyl nitrones: Application to the synthesis of the β-lactam antibiotic 1β-methylthienamycin

Author keywords

[No Author keywords available]

Indexed keywords

1BETA METHYLTHIENAMYCIN; BETA LACTAM ANTIBIOTIC; UNCLASSIFIED DRUG;

EID: 0030037595     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952254m     Document Type: Article
Times cited : (33)

References (53)
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    • American Chemical Society Arthur C. Cope Scholar, 1995.
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    • (a) Merck & Co., Inc., U.S. Patent 3 950 357 (April 12, 1976).
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    • 3643118090 scopus 로고
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    • 2Me, 77:23; Me, 84:16; Ph, 90:10. Heitkamp, H. J. Ph.D. Thesis, UCLA, 1995.
    • (1995)
    • Heitkamp, H.J.1
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    • Both N-benzyl- and N-(p-methoxybenzyl)hydroxylamine were prepared according the literature procedure: Jencks, W. P.; Maskill, H. J. Am. Chem. Soc. 1987, 109, 2062.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 2062
    • Jencks, W.P.1    Maskill, H.2
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    • (E)-5-Bromo-2-pentene was prepared according to the literature procedure: Julia, M.; Julia, S.; Tchen, S. Y. Bull. Soc. Chim. Fr. 1961, 1849. It contains ∼7% of the cis isomer which was carried through to 7c and 7d.
    • (1961) Bull. Soc. Chim. Fr. , pp. 1849
    • Julia, M.1    Julia, S.2    Tchen, S.Y.3
  • 37
    • 85033812698 scopus 로고    scopus 로고
    • note
    • The relative stereochemistry of 7b, 7d, and 14a was proven by NOESY experiments. The methyl group (not next to the oxygen, at the 6-position in the 1H-cyclopent[c]isoxazole numbering) was shown to be syn to the ring juncture hydrogens by NOESY, while the structures of 7a and 7c were assigned by analogy to 7b and 7d.
  • 39
    • 0000863940 scopus 로고
    • Padwa, A., Ed.; John Wiley & Sons, Inc.: New York
    • (b) Caramella, P.; Grunanger, P. In 1,3-Dipolar Cycloaddition; Padwa, A., Ed.; John Wiley & Sons, Inc.: New York, 1984; pp 291-392.
    • (1984) 1,3-Dipolar Cycloaddition , pp. 291-392
    • Caramella, P.1    Grunanger, P.2
  • 40
    • 0343478377 scopus 로고
    • JAI Press: Greewich, CT
    • (c) Curran, D. P. In Advances in Cycloaddition; JAI Press: Greewich, CT, 1988; Vol. 1, p 150.
    • (1988) Advances in Cycloaddition , vol.1 , pp. 150
    • Curran, D.P.1
  • 41
    • 0001287954 scopus 로고
    • (d) The structures of compounds 9 and 9′ were assigned by analogy to similar compounds reported in the literature: Hassner, A.; Murthy, K. S. K.; Padwa, A.; Chiacchio, U.; Dean, D. C.; Schoffstall, A. M. J. Org. Chem. 1989, 54, 5277. Kim, H. R.; Kim, H. J.; Duffy, J. L.; Olmstead, M. M.; Ruhlandt-Senge, K.; Kurth, M. J. Tetrahedron Lett. 1991, 32, 4259.
    • (1989) J. Org. Chem. , vol.54 , pp. 5277
    • Hassner, A.1    Murthy, K.S.K.2    Padwa, A.3    Chiacchio, U.4    Dean, D.C.5    Schoffstall, A.M.6
  • 42
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    • (d) The structures of compounds 9 and 9′ were assigned by analogy to similar compounds reported in the literature: Hassner, A.; Murthy, K. S. K.; Padwa, A.; Chiacchio, U.; Dean, D. C.; Schoffstall, A. M. J. Org. Chem. 1989, 54, 5277. Kim, H. R.; Kim, H. J.; Duffy, J. L.; Olmstead, M. M.; Ruhlandt-Senge, K.; Kurth, M. J. Tetrahedron Lett. 1991, 32, 4259.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 4259
    • Kim, H.R.1    Kim, H.J.2    Duffy, J.L.3    Olmstead, M.M.4    Ruhlandt-Senge, K.5    Kurth, M.J.6
  • 44
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    • Unpublished results
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  • 47
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    • note
    • The alcohol 13 contains ∼6-7% of the cis isomer resulting from isomerization of the double bond during ketalization, which was carried on to 14.
  • 51
    • 85033811537 scopus 로고    scopus 로고
    • note
    • In one case, with the amino being protected by the benzoyl group, only 31% of the desired ketone was obtained in p-TsOH and aqueous acetone conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.