Total synthesis of (-)-macrolactin A

Journal of the American Chemical Society

Volumn 118, Issue 51, 1996, Pages 13095-13096

  Smith III, Amos B ^a   Ott, Gregory R ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; MACROLACTIN A; MACROLIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

EID: 0030462737     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963543a     Document Type: Article

References (41)

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2. Rychnovsky, S. D.; Skalitzky, D. J.; Pathirana, C.; Jensen, P. R.; Fenical, W. J. Am. Chem. Soc. 1992, 114, 671.
3. The original bacterial source no longer produces macrolactins A-E, only macrolactin F. Fenical, W. The Scripps Institution of Oceanography, University of California, San Diego, 1995. Personal communication.
4. For a synthesis of 13,15-dimetnoxymacrolactin A, which also exploits Stille cross-coupling chemistry for key bond constructions, see: Boyce, R. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 3501.
5. For other synthetic approaches to macrolactin A and related derivatives, see: (a) Donaldson, W. A.; Bell, P. T.; Wang, Z. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA, Fall 1994; American Chemical Society: Washington, DC, 1994; ORGN 43. (b) Rychnovsky, S. D.; Pickering, D. A. Ibid.; ORGN 209. (c) Benvegnu, T.; Scio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505. (d) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829. Prahlad, V.; Donaldson, W. A. Ibid. 1996. In press, (e) Tanimori, S.; Monta, Y.; Tsubobota, M.; Makayama, M. Synth. Commun. 1996, 26, 559. (f) Benvegnu, T. J.; Toupet, L. J.; Grée, R. L. Tetrahedron 1996, 52, 11811. Benvegnu, T. J.; Grée, R. L. Ibid. 1996, 52, 11821.
6. For other synthetic approaches to macrolactin A and related derivatives, see: (a) Donaldson, W. A.; Bell, P. T.; Wang, Z. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA, Fall 1994; American Chemical Society: Washington, DC, 1994; ORGN 43. (b) Rychnovsky, S. D.; Pickering, D. A. Ibid.; ORGN 209. (c) Benvegnu, T.; Scio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505. (d) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829. Prahlad, V.; Donaldson, W. A. Ibid. 1996. In press, (e) Tanimori, S.; Monta, Y.; Tsubobota, M.; Makayama, M. Synth. Commun. 1996, 26, 559. (f) Benvegnu, T. J.; Toupet, L. J.; Grée, R. L. Tetrahedron 1996, 52, 11811. Benvegnu, T. J.; Grée, R. L. Ibid. 1996, 52, 11821.
7. For other synthetic approaches to macrolactin A and related derivatives, see: (a) Donaldson, W. A.; Bell, P. T.; Wang, Z. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA, Fall 1994; American Chemical Society: Washington, DC, 1994; ORGN 43. (b) Rychnovsky, S. D.; Pickering, D. A. Ibid.; ORGN 209. (c) Benvegnu, T.; Scio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505. (d) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829. Prahlad, V.; Donaldson, W. A. Ibid. 1996. In press, (e) Tanimori, S.; Monta, Y.; Tsubobota, M.; Makayama, M. Synth. Commun. 1996, 26, 559. (f) Benvegnu, T. J.; Toupet, L. J.; Grée, R. L. Tetrahedron 1996, 52, 11811. Benvegnu, T. J.; Grée, R. L. Ibid. 1996, 52, 11821.
8. For other synthetic approaches to macrolactin A and related derivatives, see: (a) Donaldson, W. A.; Bell, P. T.; Wang, Z. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA, Fall 1994; American Chemical Society: Washington, DC, 1994; ORGN 43. (b) Rychnovsky, S. D.; Pickering, D. A. Ibid.; ORGN 209. (c) Benvegnu, T.; Scio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505. (d) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829. Prahlad, V.; Donaldson, W. A. Ibid. 1996. In press, (e) Tanimori, S.; Monta, Y.; Tsubobota, M.; Makayama, M. Synth. Commun. 1996, 26, 559. (f) Benvegnu, T. J.; Toupet, L. J.; Grée, R. L. Tetrahedron 1996, 52, 11811. Benvegnu, T. J.; Grée, R. L. Ibid. 1996, 52, 11821.
9. For other synthetic approaches to macrolactin A and related derivatives, see: (a) Donaldson, W. A.; Bell, P. T.; Wang, Z. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA, Fall 1994; American Chemical Society: Washington, DC, 1994; ORGN 43. (b) Rychnovsky, S. D.; Pickering, D. A. Ibid.; ORGN 209. (c) Benvegnu, T.; Scio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505. (d) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829. Prahlad, V.; Donaldson, W. A. Ibid. 1996. In press, (e) Tanimori, S.; Monta, Y.; Tsubobota, M.; Makayama, M. Synth. Commun. 1996, 26, 559. (f) Benvegnu, T. J.; Toupet, L. J.; Grée, R. L. Tetrahedron 1996, 52, 11811. Benvegnu, T. J.; Grée, R. L. Ibid. 1996, 52, 11821.
10. For other synthetic approaches to macrolactin A and related derivatives, see: (a) Donaldson, W. A.; Bell, P. T.; Wang, Z. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA, Fall 1994; American Chemical Society: Washington, DC, 1994; ORGN 43. (b) Rychnovsky, S. D.; Pickering, D. A. Ibid.; ORGN 209. (c) Benvegnu, T.; Scio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505. (d) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829. Prahlad, V.; Donaldson, W. A. Ibid. 1996. In press, (e) Tanimori, S.; Monta, Y.; Tsubobota, M.; Makayama, M. Synth. Commun. 1996, 26, 559. (f) Benvegnu, T. J.; Toupet, L. J.; Grée, R. L. Tetrahedron 1996, 52, 11811. Benvegnu, T. J.; Grée, R. L. Ibid. 1996, 52, 11821.
11. For other synthetic approaches to macrolactin A and related derivatives, see: (a) Donaldson, W. A.; Bell, P. T.; Wang, Z. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA, Fall 1994; American Chemical Society: Washington, DC, 1994; ORGN 43. (b) Rychnovsky, S. D.; Pickering, D. A. Ibid.; ORGN 209. (c) Benvegnu, T.; Scio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505. (d) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829. Prahlad, V.; Donaldson, W. A. Ibid. 1996. In press, (e) Tanimori, S.; Monta, Y.; Tsubobota, M.; Makayama, M. Synth. Commun. 1996, 26, 559. (f) Benvegnu, T. J.; Toupet, L. J.; Grée, R. L. Tetrahedron 1996, 52, 11811. Benvegnu, T. J.; Grée, R. L. Ibid. 1996, 52, 11821.
12. For other synthetic approaches to macrolactin A and related derivatives, see: (a) Donaldson, W. A.; Bell, P. T.; Wang, Z. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA, Fall 1994; American Chemical Society: Washington, DC, 1994; ORGN 43. (b) Rychnovsky, S. D.; Pickering, D. A. Ibid.; ORGN 209. (c) Benvegnu, T.; Scio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505. (d) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829. Prahlad, V.; Donaldson, W. A. Ibid. 1996. In press, (e) Tanimori, S.; Monta, Y.; Tsubobota, M.; Makayama, M. Synth. Commun. 1996, 26, 559. (f) Benvegnu, T. J.; Toupet, L. J.; Grée, R. L. Tetrahedron 1996, 52, 11811. Benvegnu, T. J.; Grée, R. L. Ibid. 1996, 52, 11821.
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14. To our knowledge. Stille was the first to employ his palladium-catalyzed cross-coupling for macrolide construction: Stille, J. K.; Tanaka, M. J. Am. Chem. Soc. 1987, 109, 2785. Also see: Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. Nicolaou elegantly extended this methodology by employing a Stille-type "stitching-cyclization" to install the C(19)-C(20) vinyl unit and close the macrocycle in rapamycin: Nicolaou, K. C.; Chakraborty, T. K.; Piscopio, A. D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc. 1993, 115, 4419.
15. To our knowledge. Stille was the first to employ his palladium-catalyzed cross-coupling for macrolide construction: Stille, J. K.; Tanaka, M. J. Am. Chem. Soc. 1987, 109, 2785. Also see: Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. Nicolaou elegantly extended this methodology by employing a Stille-type "stitching-cyclization" to install the C(19)-C(20) vinyl unit and close the macrocycle in rapamycin: Nicolaou, K. C.; Chakraborty, T. K.; Piscopio, A. D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc. 1993, 115, 4419.
16. To our knowledge. Stille was the first to employ his palladium-catalyzed cross-coupling for macrolide construction: Stille, J. K.; Tanaka, M. J. Am. Chem. Soc. 1987, 109, 2785. Also see: Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. Nicolaou elegantly extended this methodology by employing a Stille-type "stitching-cyclization" to install the C(19)-C(20) vinyl unit and close the macrocycle in rapamycin: Nicolaou, K. C.; Chakraborty, T. K.; Piscopio, A. D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc. 1993, 115, 4419.
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41. 13C NMR spectra of 1.