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Volumn 37, Issue 19, 1998, Pages 2700-2704

Total syntheses of vancomycin and eremomycin aglycons

Author keywords

Antibiotics; Eremomycin; Natural products; Total synthesis; Vancomycin

Indexed keywords


EID: 0032538575     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P     Document Type: Article
Times cited : (283)

References (47)
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    • D. A. Evans, K. D. DeVries in ref. [2], pp. 63-103
    • For reviews on methodology relevant to the synthesis of the vancomycin aglycon structure see: a) D. A. Evans, K. D. DeVries in ref. [2], pp. 63-103; b) A. V. Rama Rao, M. K. Gurjar, K. L. Reddy, A. S. Rao, Chem. Rev. 1995, 95, 2135-2168; c) J. Zhu, Synlett. 1997, 133-144; d) R. M. Williams, J. A. Hendrix, Chem. Rev. 1992, 92, 889-917.
  • 9
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    • For reviews on methodology relevant to the synthesis of the vancomycin aglycon structure see: a) D. A. Evans, K. D. DeVries in ref. [2], pp. 63-103; b) A. V. Rama Rao, M. K. Gurjar, K. L. Reddy, A. S. Rao, Chem. Rev. 1995, 95, 2135-2168; c) J. Zhu, Synlett. 1997, 133-144; d) R. M. Williams, J. A. Hendrix, Chem. Rev. 1992, 92, 889-917.
    • (1995) Chem. Rev. , vol.95 , pp. 2135-2168
    • Rama Rao, A.V.1    Gurjar, M.K.2    Reddy, K.L.3    Rao, A.S.4
  • 10
    • 1542527790 scopus 로고    scopus 로고
    • For reviews on methodology relevant to the synthesis of the vancomycin aglycon structure see: a) D. A. Evans, K. D. DeVries in ref. [2], pp. 63-103; b) A. V. Rama Rao, M. K. Gurjar, K. L. Reddy, A. S. Rao, Chem. Rev. 1995, 95, 2135-2168; c) J. Zhu, Synlett. 1997, 133-144; d) R. M. Williams, J. A. Hendrix, Chem. Rev. 1992, 92, 889-917.
    • (1997) Synlett. , pp. 133-144
    • Zhu, J.1
  • 11
    • 0001122927 scopus 로고
    • For reviews on methodology relevant to the synthesis of the vancomycin aglycon structure see: a) D. A. Evans, K. D. DeVries in ref. [2], pp. 63-103; b) A. V. Rama Rao, M. K. Gurjar, K. L. Reddy, A. S. Rao, Chem. Rev. 1995, 95, 2135-2168; c) J. Zhu, Synlett. 1997, 133-144; d) R. M. Williams, J. A. Hendrix, Chem. Rev. 1992, 92, 889-917.
    • (1992) Chem. Rev. , vol.92 , pp. 889-917
    • Williams, R.M.1    Hendrix, J.A.2
  • 12
    • 0345570538 scopus 로고    scopus 로고
    • note
    • p: (4S)-4-(phenylmethyl)-2-oxazolidinone; Tfa: trifluoroacetyl TFA: trifluoroacetic acid; Boc: tert-butoxycarbonyl; NOE: nuclear Overhauser effect; Tf: trifluoromethanesulfonyl; Ms: methanesulfonyl; Bn: benzyl; Piv: pivaloyl; Ddm: 4,4′dimethoxydiphenylmethyl; EDCI · HCl: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride; HOBt: 1-hydroxybenzotriazole; DMAP: 4-dimethylaminopyridine; DMS: dimethylsulfide; TFAA: trifluoroacetic anhydride; HATU: O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate; HOAt: 7-aza-1-hydroxybenzotriazole; LDA: lithium diisopropylamide; dppf: 1,1′-bis(diphenylphosphanyl)ferrocene.
  • 21
    • 0030920928 scopus 로고    scopus 로고
    • For the synthesis of orienticin C aglycon see: a) D. A. Evans, C. J. Dinsmore, A. M. Ratz, D. A. Evrard, J. C. Barrow, J. Am. Chem. Soc. 1997, 119, 3417-3418; b) D. A. Evans, J. C Barrow, P. S. Watson, A. M. Ratz, C. J. Dinsmore, D. A. Evrard, K. M. DeVries, J. A. Ellman, S. D. Rychnovsky, J. Lacour, J. Am. Chem. Soc. 1997, 119, 3419-3420.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 3417-3418
    • Evans, D.A.1    Dinsmore, C.J.2    Ratz, A.M.3    Evrard, D.A.4    Barrow, J.C.5
  • 24
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    • D. A. Evans, C. J. Dinsmore, P. S. Watson, M. R. Wood, T. I. Richardson, B. W. Trotter, J. L. Katz, Angew. Chem. 1998, 111, 2868-2872; Angew. Chem. Int. Ed. 1998, 37, 2704-2708.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 2704-2708
  • 25
    • 0344708510 scopus 로고    scopus 로고
    • note
    • The seven amino acid residues are numbered consecutively starting from the amino terminus. The M(X-Y) nomenclature refers to the macrocycle containing an oxidative cross-link between aryl groups of residues X and Y. Bicyclic moieties will be identified as M(W-Y)(X-Z).
  • 26
    • 0345139008 scopus 로고    scopus 로고
    • note
    • Amino acid 4 was derived from (R)-para-hydroxy-phenylglycine.
  • 27
    • 0008495409 scopus 로고
    • Compound 4b was prepared by the chlorination of 4a: F. D. March, W. B. Farnham, D. J. Sam, B. E. Smart, J. Am. Chem. Soc. 1982, 104, 4680-4682. 4-Fluoro-3-nitrobenzaldehyde (4a) was prepared from 4-fluorobenzaldehyde: F. Michael, D. Noffz, Chem. Ber. 1957, 90, 1586-1589. Dr. S. Rubenstein is acknowledged for the preparation of this material.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 4680-4682
    • March, F.D.1    Farnham, W.B.2    Sam, D.J.3    Smart, B.E.4
  • 28
    • 0011962156 scopus 로고
    • Compound 4b was prepared by the chlorination of 4a: F. D. March, W. B. Farnham, D. J. Sam, B. E. Smart, J. Am. Chem. Soc. 1982, 104, 4680-4682. 4-Fluoro-3-nitrobenzaldehyde (4a) was prepared from 4-fluorobenzaldehyde: F. Michael, D. Noffz, Chem. Ber. 1957, 90, 1586-1589. Dr. S. Rubenstein is acknowledged for the preparation of this material.
    • (1957) Chem. Ber. , vol.90 , pp. 1586-1589
    • Michael, F.1    Noffz, D.2
  • 29
    • 0001597804 scopus 로고
    • Alternate conditions and reagents were plagued by competitive endocyclic oxazolidinone hydrolysis and/or undesired nucleophilic displacement of the fluoride. D. A. Evans, T. C. Britton, J. A. Ellman, Tetrahedron Lett. 1987, 28, 6141-6144.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 6141-6144
    • Evans, D.A.1    Britton, T.C.2    Ellman, J.A.3
  • 31
    • 0345570535 scopus 로고    scopus 로고
    • note
    • The removal of the TBS protecting group highlighted the significant reactivity difference between the chloro and des-chloro substrates. Treatment of 13b with TBAF resulted in immediate M(4-6) cyclization with reduced diastereoselection. See also ref. [24].
  • 32
    • 0345570534 scopus 로고    scopus 로고
    • note
    • 3) in favor of the unnatural atropisomer. It was further observed that cyclization of substrates in which the meta-phenols of amino acid 4 were both unmasked proceeded with negligible selectivity under a variety of conditions, necessitating the synthesis of a fully differentiated triphenol.
  • 33
    • 0344276494 scopus 로고    scopus 로고
    • note
    • 1H NMR, HPLC, and mass spectral data identical to a natural comparison sample (refs. [23] and [27]).
  • 34
    • 0344276495 scopus 로고    scopus 로고
    • note
    • We thank Mr. Kevin Campos for determining the X-ray structure of this intermediate.
  • 36
    • 0345570533 scopus 로고    scopus 로고
    • note
    • This assignment was confirmed by chemical correlation to a minor atropisomer corresponding to 16.
  • 38
    • 0345570532 scopus 로고    scopus 로고
    • note
    • Separation of the undesired M(4-6) atropisomer was most conveniently achieved at this stage; the desired isomer was isolated in 69% yield.
  • 39
    • 0344276493 scopus 로고    scopus 로고
    • note
    • The stereochemistry of 20 was confirmed by ROESY analysis (500 MHz).
  • 44
    • 0344276492 scopus 로고    scopus 로고
    • note
    • We thank Dr. Bret Huff of Eli Lilly & Company for generous samples of vancomycin · HCl and eremomcyin · HOAc.
  • 45
    • 0023676889 scopus 로고
    • Vancomycin aglycon was prepared from vancomycin · HCl according to: R. Nagarajan, A. A. Schabel, J. Chem. Soc. Chem. Comm. 1988, 1306-1307; see also F. J. Marshall, J. Med. Chem. 1965, 8, 18-24.
    • (1988) J. Chem. Soc. Chem. Comm. , pp. 1306-1307
    • Nagarajan, R.1    Schabel, A.A.2
  • 46
    • 0002609435 scopus 로고
    • Vancomycin aglycon was prepared from vancomycin · HCl according to: R. Nagarajan, A. A. Schabel, J. Chem. Soc. Chem. Comm. 1988, 1306-1307; see also F. J. Marshall, J. Med. Chem. 1965, 8, 18-24.
    • (1965) J. Med. Chem. , vol.8 , pp. 18-24
    • Marshall, F.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.