-
1
-
-
0003793630
-
-
M. H. McCormick, W. M. Stark, G. E. Pittenger, R. C. Pittenger, G. M. McGuire, Antibiot. Annu. 1955-56, 606-611.
-
(1955)
Antibiot. Annu.
, pp. 606-611
-
-
McCormick, M.H.1
Stark, W.M.2
Pittenger, G.E.3
Pittenger, R.C.4
McGuire, G.M.5
-
2
-
-
0004305786
-
-
Marcel Dekker, New York
-
For a comprehensive discussion of the vancomycin antibiotics see: Glycopeptide Antibiotics (Ed.: R. Nagarajan), Marcel Dekker, New York, 1994.
-
(1994)
Glycopeptide Antibiotics
-
-
Nagarajan, R.1
-
4
-
-
0020698393
-
-
b) M. Foldes, R. Munro, T. C. Sorrell, S. Shankar, M. Toohey, J. Antimicrob. Chemother. 1983, 11, 21-26.
-
(1983)
J. Antimicrob. Chemother.
, vol.11
, pp. 21-26
-
-
Foldes, M.1
Munro, R.2
Sorrell, T.C.3
Shankar, S.4
Toohey, M.5
-
5
-
-
0031566833
-
-
a) S. Tabaqchali, Lancet, 1997, 350, 1644-1645;
-
(1997)
Lancet
, vol.350
, pp. 1644-1645
-
-
Tabaqchali, S.1
-
7
-
-
0029678259
-
-
and references therein
-
c) C. T. Walsh, S. L. Fisher, I.-S. Park, M. Prahalad, Z. Wu, Chem. Biol. 1996, 3, 21-28, and references therein.
-
(1996)
Chem. Biol.
, vol.3
, pp. 21-28
-
-
Walsh, C.T.1
Fisher, S.L.2
Park, I.-S.3
Prahalad, M.4
Wu, Z.5
-
8
-
-
0345570540
-
-
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
-
-
4243924840
-
-
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
-
-
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
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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.
-
(1992)
Chem. Rev.
, vol.92
, pp. 889-917
-
-
Williams, R.M.1
Hendrix, J.A.2
-
12
-
-
0345570538
-
-
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.
-
-
-
-
13
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0026500175
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-
a) D. A. Evans, D. A. Evrard, S. D. Rychnovsky, T. Früh, W. G. Wittingham, K. M. DeVries, Tetrahedron Lett. 1992, 33, 1189-1192;
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 1189-1192
-
-
Evans, D.A.1
Evrard, D.A.2
Rychnovsky, S.D.3
Früh, T.4
Wittingham, W.G.5
DeVries, K.M.6
-
14
-
-
0025324609
-
-
b) D. A. Evans, T. C. Britton, J. A. Ellman, R. L. Dorow, J. Am. Chem. Soc. 1990, 112, 4011-4030;
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 4011-4030
-
-
Evans, D.A.1
Britton, T.C.2
Ellman, J.A.3
Dorow, R.L.4
-
16
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-
0024802535
-
-
a) D. A. Evans, J. A. Ellman, K. M. DeVries, J. Am. Chem. Soc. 1989, 111, 8912-8914;
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 8912-8914
-
-
Evans, D.A.1
Ellman, J.A.2
DeVries, K.M.3
-
17
-
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0030942291
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-
b) D. A. Evans, C. J. Dinsmore, A. M. Ratz,Tetrahedron Lett. 1997, 38, 3189-3192;
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 3189-3192
-
-
Evans, D.A.1
Dinsmore, C.J.2
Ratz, A.M.3
-
19
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0027274921
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a) D. A. Evans, C. J. Dinsmore, D. A. Evrard, K. M. DeVries, J. Am. Chem. Soc. 1993, 115, 6426-6427;
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 6426-6427
-
-
Evans, D.A.1
Dinsmore, C.J.2
Evrard, D.A.3
DeVries, K.M.4
-
21
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0030920928
-
-
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
-
22
-
-
0031009133
-
-
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. 3419-3420
-
-
Evans, D.A.1
Barrow, J.C.2
Watson, P.S.3
Ratz, A.M.4
Dinsmore, C.J.5
Evrard, D.A.6
DeVries, K.M.7
Ellman, J.A.8
Rychnovsky, S.D.9
Lacour, J.10
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23
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0001525716
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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.
, vol.111
, pp. 2868-2872
-
-
Evans, D.A.1
Dinsmore, C.J.2
Watson, P.S.3
Wood, M.R.4
Richardson, T.I.5
Trotter, B.W.6
Katz, J.L.7
-
24
-
-
0032538360
-
-
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
-
-
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
-
-
note
-
Amino acid 4 was derived from (R)-para-hydroxy-phenylglycine.
-
-
-
-
27
-
-
0008495409
-
-
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
-
-
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
-
-
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
-
30
-
-
33845312505
-
-
HATU-mediated peptide coupling: L. A. Carpino, A. El-Fahan, C. A. Minor, F Albericio, J. Chem. Soc. Chem. Commun. 1994, 201-203.
-
(1994)
J. Chem. Soc. Chem. Commun.
, pp. 201-203
-
-
Carpino, L.A.1
El-Fahan, A.2
Minor, C.A.3
Albericio, F.4
-
31
-
-
0345570535
-
-
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
-
-
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
-
-
note
-
1H NMR, HPLC, and mass spectral data identical to a natural comparison sample (refs. [23] and [27]).
-
-
-
-
34
-
-
0344276495
-
-
note
-
We thank Mr. Kevin Campos for determining the X-ray structure of this intermediate.
-
-
-
-
36
-
-
0345570533
-
-
note
-
This assignment was confirmed by chemical correlation to a minor atropisomer corresponding to 16.
-
-
-
-
37
-
-
0001642236
-
-
S. Cacci, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 1986, 27, 5541-5544.
-
(1986)
Tetrahedron Lett.
, vol.27
, pp. 5541-5544
-
-
Cacci, S.1
Ciattini, P.G.2
Morera, E.3
Ortar, G.4
-
38
-
-
0345570532
-
-
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
-
-
note
-
The stereochemistry of 20 was confirmed by ROESY analysis (500 MHz).
-
-
-
-
40
-
-
0030805117
-
-
D. L. Boger, R. M. Borzilleri, S. Nukui, R. T. Beresis, J. Org. Chem. 1997, 62, 4721-4736.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 4721-4736
-
-
Boger, D.L.1
Borzilleri, R.M.2
Nukui, S.3
Beresis, R.T.4
-
41
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-
0030912448
-
-
D. A. Evans, P. H. Carter, C. J. Dinsmore, J. C. Barrow, J. L. Katz, D. W. Kung, Tetrahedron Lett. 1997, 38, 4535-4538.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 4535-4538
-
-
Evans, D.A.1
Carter, P.H.2
Dinsmore, C.J.3
Barrow, J.C.4
Katz, J.L.5
Kung, D.W.6
-
42
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0001587728
-
-
J. Garcia, J. Gonzalez, R. Segura, J. Vilarrasa, Tetrahedron 1984, 40, 3121-3127.
-
(1984)
Tetrahedron
, vol.40
, pp. 3121-3127
-
-
Garcia, J.1
Gonzalez, J.2
Segura, R.3
Vilarrasa, J.4
-
43
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0001021477
-
-
A. M. Felix, E. P. Heimer, T. J. Lambros, C. Tzougraki, J. Meienhofer, J. Org. Chem. 1978, 43, 4194-4196.
-
(1978)
J. Org. Chem.
, vol.43
, pp. 4194-4196
-
-
Felix, A.M.1
Heimer, E.P.2
Lambros, T.J.3
Tzougraki, C.4
Meienhofer, J.5
-
44
-
-
0344276492
-
-
note
-
We thank Dr. Bret Huff of Eli Lilly & Company for generous samples of vancomycin · HCl and eremomcyin · HOAc.
-
-
-
-
45
-
-
0023676889
-
-
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
-
-
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
-
47
-
-
0024841935
-
-
Eremomycin aglycon was prepared from eremomycin · HOAc according to: G. F. Gause, M. G. Brazhnikova, N. N. Lomakina, T. F. Berdnikova, G. B. Fedorova, N. L. Tokareva, V. N. Borisova, G. Y. Batta, J. Antibiotics 1989, 42, 1790-1799.
-
(1989)
J. Antibiotics
, vol.42
, pp. 1790-1799
-
-
Gause, G.F.1
Brazhnikova, M.G.2
Lomakina, N.N.3
Berdnikova, T.F.4
Fedorova, G.B.5
Tokareva, N.L.6
Borisova, V.N.7
Batta, G.Y.8
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