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Volumn 124, Issue 50, 2002, Pages 15001-15005

Total synthesis of desferrisalmycin B

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FIRST TOTAL SYNTHESIS;

EID: 0037132597     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028386w     Document Type: Article
Times cited : (43)

References (51)
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    • Grindley, T.B.1    Thangarasa, R.2
  • 23
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    • 2 hydrochloride and the subsequent protection of the amino group with a Boc group, the nitrile could not be reduced to the corresponding aldehyde under various conditions.
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  • 24
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    • 2 hydrochloride and the subsequent protection of the amino group with a Boc group, the nitrile could not be reduced to the corresponding aldehyde under various conditions.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 3879
    • Arndt, H.1    Polborn, K.2    Koert, U.3
  • 25
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    • 2 hydrochloride and the subsequent protection of the amino group with a Boc group, the nitrile could not be reduced to the corresponding aldehyde under various conditions.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 1085
    • Brown, H.C.1    Garg, C.P.2
  • 26
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    • (a) Hashimoto, H.; Asano, K.; Fujii, F.; Yoshimura, J. Carbohydr. Res. 1982, 104, 87. (b) Effenberger, F.; Stelzer, U. Tetrahedron: Asymmetry 1995, 6, 283. The aziridine was prepared in less than 10% yield from the cyanohydrin of aldehyde 15 due to the reductive cleavage of the mesylate by LAH. The Lewis acid-mediated aziridine opening by benzyl alcohol also failed.
    • (1982) Carbohydr. Res. , vol.104 , pp. 87
    • Hashimoto, H.1    Asano, K.2    Fujii, F.3    Yoshimura, J.4
  • 27
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    • (a) Hashimoto, H.; Asano, K.; Fujii, F.; Yoshimura, J. Carbohydr. Res. 1982, 104, 87. (b) Effenberger, F.; Stelzer, U. Tetrahedron: Asymmetry 1995, 6, 283. The aziridine was prepared in less than 10% yield from the cyanohydrin of aldehyde 15 due to the reductive cleavage of the mesylate by LAH. The Lewis acid-mediated aziridine opening by benzyl alcohol also failed.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 283
    • Effenberger, F.1    Stelzer, U.2
  • 30
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    • (a) van Delft, F.; de Kort, M.; van der Marel, G. A.; van Boom, J. H. Tetrahedron: Asymmetry 1994, 5, 2261. (b) Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; Kamijo, T.; Harada, H.; Terashima, S. Tetrahedron Lett. 1990, 31, 4175. The addition of organometallic phenyldimethylsilylmethyl reagents (magnesium or cerium) to aldehyde 15 or aldimine prepared from 15 and methylamine failed to generate the desired products.
    • (1994) Tetrahedron: Asymmetry , vol.5 , pp. 2261
    • Van Delft, F.1    De Kort, M.2    Van der Marel, G.A.3    Van Boom, J.H.4
  • 31
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    • (a) van Delft, F.; de Kort, M.; van der Marel, G. A.; van Boom, J. H. Tetrahedron: Asymmetry 1994, 5, 2261. (b) Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; Kamijo, T.; Harada, H.; Terashima, S. Tetrahedron Lett. 1990, 31, 4175. The addition of organometallic phenyldimethylsilylmethyl reagents (magnesium or cerium) to aldehyde 15 or aldimine prepared from 15 and methylamine failed to generate the desired products.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 4175
    • Matsumoto, T.1    Kobayashi, Y.2    Takemoto, Y.3    Ito, Y.4    Kamijo, T.5    Harada, H.6    Terashima, S.7
  • 44
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    • note
    • 13C NMR of compound 23 indicated that the newly formed resonance was at 94.48 ppm with a coupling constant of 170.35 Hz.
  • 45
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    • Ph.D. Thesis, University of Notre Dame
    • McKee, J. A. Ph.D. Thesis, University of Notre Dame, 1991.
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    • Bessodes, M.; Dubertret, C.; Jasin, G.; Scherman, D. Bioorg. Med. Chem. Lett. 2000, 10, 1393. Alternatively, the E-oxime was prepared as a protected carbonyl compound (Barili, P. L.; Berti. G.; D'Andrea, F.; Di Bussolo, V. Carbohydr. Res. 1996, 290, 17). This also provided an easy entry to salmycin A. Unfortunately, although the silyl ether deprotection and acylation could be conducted without incident to afford the desired acid, the final coupling reaction with compound 28 failed to afford the desired product.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 1393
    • Bessodes, M.1    Dubertret, C.2    Jasin, G.3    Scherman, D.4
  • 49
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    • Bessodes, M.; Dubertret, C.; Jasin, G.; Scherman, D. Bioorg. Med. Chem. Lett. 2000, 10, 1393. Alternatively, the E-oxime was prepared as a protected carbonyl compound (Barili, P. L.; Berti. G.; D'Andrea, F.; Di Bussolo, V. Carbohydr. Res. 1996, 290, 17). This also provided an easy entry to salmycin A. Unfortunately, although the silyl ether deprotection and acylation could be conducted without incident to afford the desired acid, the final coupling reaction with compound 28 failed to afford the desired product.
    • (1996) Carbohydr. Res. , vol.290 , pp. 17
    • Barili, P.L.1    Berti, G.2    D'Andrea, F.3    Di Bussolo, V.4
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    • note
    • The siderophore conjugate was prepared with the 2′-hydroxyl group protected with an acetyl group. However. deacetylation caused the simultaneous cleavage of the ester linkage.
  • 51
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    • note
    • Although the coupling reaction of acid 31 and compound 28 afforded the desired conjugate, this compound was too sensitive to survive the DDQ-mediated PMB deprotection.


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