Total synthesis of the ansamycin antibiotic (+)-thiazinotrienomycin E

Journal of Organic Chemistry

Volumn 65, Issue 12, 2000, Pages 3738-3753

  Smith III, Amos B ^a   Wan, Zehong ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANSAMYCIN DERIVATIVE; THIAZINOTRIENOMYCIN E; UNCLASSIFIED DRUG;

ANTIBIOTIC THERAPY; ARTICLE; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; CHEMISTRY, ORGANIC; INDICATORS AND REAGENTS; STREPTOMYCES; SULFONES; THIAZINES;

EID: 0034674416     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991958j     Document Type: Article

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6. Smith, A. B., III; Wood, J. L.; Wong, W.; Gould, A. E.; Rizzo, C. J.; Barbosa, J.; Komiyama, K.; Ōmura, S. J. Am. Chem. Soc. 1996, 118, 8308-8315. Smith, A. B., III; Barbosa, J.; Wong, W.; Wood, J. L. J. Am. Chem. Soc. 1996, 118, 8316-8328. Smith, A. B., III; Barbosa, J.; Wong, W.; Wood, J. L. J. Am. Chem. Soc. 1995, 117, 10777-10778. Smith, A. B., III; Wood, J. L.; Gould, A. E.; Ōmura, S.; Komiyama, K. Tetrahedron Lett. 1991, 32, 1627-1630. Smith, A. B., III; Wood, J. L.; Ōmura, S. Tetrahedron Lett. 1991, 32, 841-842. Smith, A. B., III; Wood, J. L.; Wong, W.; Gould, A. E.; Rizzo, C. J.; Funayama, S.; Ōmura, S. J. Am. Chem. Soc. 1990, 112, 7425-7426. For other synthetic approaches to the trienomycins and related mycotrienins, see: Masse, C. E.; Yang, M.; Solomon, J.; Panek, J. S. J. Am. Chem. Soc. 1998, 120, 4123-4134. Yadav, J. S.; Praveen Kumar, T. K.; Maniyan, P. P. Tetrahedron Lett. 1993, 34, 2965-2968. Fürstner, A.; Baumgartner, J. Tetrahedron 1993, 49, 8541-8560. Schoning, K. U.; Hayashi, R. K.; Powell, D. R.; Kirschning, A. Tetrahedron: Asymmetry 1999, 10, 817- 820. Schoning, K. U.; Wittenberg, R.; Kirschning, A. Synlett 1999, 1624-1626.
7. Smith, A. B., III; Wood, J. L.; Wong, W.; Gould, A. E.; Rizzo, C. J.; Barbosa, J.; Komiyama, K.; Ōmura, S. J. Am. Chem. Soc. 1996, 118, 8308-8315. Smith, A. B., III; Barbosa, J.; Wong, W.; Wood, J. L. J. Am. Chem. Soc. 1996, 118, 8316-8328. Smith, A. B., III; Barbosa, J.; Wong, W.; Wood, J. L. J. Am. Chem. Soc. 1995, 117, 10777-10778. Smith, A. B., III; Wood, J. L.; Gould, A. E.; Ōmura, S.; Komiyama, K. Tetrahedron Lett. 1991, 32, 1627-1630. Smith, A. B., III; Wood, J. L.; Ōmura, S. Tetrahedron Lett. 1991, 32, 841-842. Smith, A. B., III; Wood, J. L.; Wong, W.; Gould, A. E.; Rizzo, C. J.; Funayama, S.; Ōmura, S. J. Am. Chem. Soc. 1990, 112, 7425-7426. For other synthetic approaches to the trienomycins and related mycotrienins, see: Masse, C. E.; Yang, M.; Solomon, J.; Panek, J. S. J. Am. Chem. Soc. 1998, 120, 4123-4134. Yadav, J. S.; Praveen Kumar, T. K.; Maniyan, P. P. Tetrahedron Lett. 1993, 34, 2965-2968. Fürstner, A.; Baumgartner, J. Tetrahedron 1993, 49, 8541-8560. Schoning, K. U.; Hayashi, R. K.; Powell, D. R.; Kirschning, A. Tetrahedron: Asymmetry 1999, 10, 817- 820. Schoning, K. U.; Wittenberg, R.; Kirschning, A. Synlett 1999, 1624-1626.
8. Smith, A. B., III; Wood, J. L.; Wong, W.; Gould, A. E.; Rizzo, C. J.; Barbosa, J.; Komiyama, K.; Ōmura, S. J. Am. Chem. Soc. 1996, 118, 8308-8315. Smith, A. B., III; Barbosa, J.; Wong, W.; Wood, J. L. J. Am. Chem. Soc. 1996, 118, 8316-8328. Smith, A. B., III; Barbosa, J.; Wong, W.; Wood, J. L. J. Am. Chem. Soc. 1995, 117, 10777-10778. Smith, A. B., III; Wood, J. L.; Gould, A. E.; Ōmura, S.; Komiyama, K. Tetrahedron Lett. 1991, 32, 1627-1630. Smith, A. B., III; Wood, J. L.; Ōmura, S. Tetrahedron Lett. 1991, 32, 841-842. Smith, A. B., III; Wood, J. L.; Wong, W.; Gould, A. E.; Rizzo, C. J.; Funayama, S.; Ōmura, S. J. Am. Chem. Soc. 1990, 112, 7425-7426. For other synthetic approaches to the trienomycins and related mycotrienins, see: Masse, C. E.; Yang, M.; Solomon, J.; Panek, J. S. J. Am. Chem. Soc. 1998, 120, 4123-4134. Yadav, J. S.; Praveen Kumar, T. K.; Maniyan, P. P. Tetrahedron Lett. 1993, 34, 2965-2968. Fürstner, A.; Baumgartner, J. Tetrahedron 1993, 49, 8541-8560. Schoning, K. U.; Hayashi, R. K.; Powell, D. R.; Kirschning, A. Tetrahedron: Asymmetry 1999, 10, 817- 820. Schoning, K. U.; Wittenberg, R.; Kirschning, A. Synlett 1999, 1624-1626.
9. Smith, A. B., III; Wood, J. L.; Wong, W.; Gould, A. E.; Rizzo, C. J.; Barbosa, J.; Komiyama, K.; Ōmura, S. J. Am. Chem. Soc. 1996, 118, 8308-8315. Smith, A. B., III; Barbosa, J.; Wong, W.; Wood, J. L. J. Am. Chem. Soc. 1996, 118, 8316-8328. Smith, A. B., III; Barbosa, J.; Wong, W.; Wood, J. L. J. Am. Chem. Soc. 1995, 117, 10777-10778. Smith, A. B., III; Wood, J. L.; Gould, A. E.; Ōmura, S.; Komiyama, K. Tetrahedron Lett. 1991, 32, 1627-1630. Smith, A. B., III; Wood, J. L.; Ōmura, S. Tetrahedron Lett. 1991, 32, 841-842. Smith, A. B., III; Wood, J. L.; Wong, W.; Gould, A. E.; Rizzo, C. J.; Funayama, S.; Ōmura, S. J. Am. Chem. Soc. 1990, 112, 7425-7426. For other synthetic approaches to the trienomycins and related mycotrienins, see: Masse, C. E.; Yang, M.; Solomon, J.; Panek, J. S. J. Am. Chem. Soc. 1998, 120, 4123-4134. Yadav, J. S.; Praveen Kumar, T. K.; Maniyan, P. P. Tetrahedron Lett. 1993, 34, 2965-2968. Fürstner, A.; Baumgartner, J. Tetrahedron 1993, 49, 8541-8560. Schoning, K. U.; Hayashi, R. K.; Powell, D. R.; Kirschning, A. Tetrahedron: Asymmetry 1999, 10, 817- 820. Schoning, K. U.; Wittenberg, R.; Kirschning, A. Synlett 1999, 1624-1626.
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36. Interestingly, the aldehyde was also reduced under these conditions.
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41. Blakemore, P. R.; Cole, W. J.; Kocienski, P. J.; Morley, A. Synlett 1998, 1, 26-28. For recent applications of this reaction in synthesis, see: Blakemore, P. R.; Kocienski, P. J.; Morley, A.; Muir, K. J. Chem. Soc., Perkin Trans. 1 1999, 955-968. Williams, D. R.; Brooks, D. A.; Berliner, M. A. J. Am. Chem. Soc. 1999, 121, 4924-4925. Williams, D. R. Clark, M. P. Tetrahedron Lett. 1999, 40, 2291-2294. Metternich, R.; Denni, D.; Thai, B.; Sedrani, R. J. Org. Chem. 1999, 64, 9632- 9639.
42. Blakemore, P. R.; Cole, W. J.; Kocienski, P. J.; Morley, A. Synlett 1998, 1, 26-28. For recent applications of this reaction in synthesis, see: Blakemore, P. R.; Kocienski, P. J.; Morley, A.; Muir, K. J. Chem. Soc., Perkin Trans. 1 1999, 955-968. Williams, D. R.; Brooks, D. A.; Berliner, M. A. J. Am. Chem. Soc. 1999, 121, 4924-4925. Williams, D. R. Clark, M. P. Tetrahedron Lett. 1999, 40, 2291-2294. Metternich, R.; Denni, D.; Thai, B.; Sedrani, R. J. Org. Chem. 1999, 64, 9632- 9639.
43. Blakemore, P. R.; Cole, W. J.; Kocienski, P. J.; Morley, A. Synlett 1998, 1, 26-28. For recent applications of this reaction in synthesis, see: Blakemore, P. R.; Kocienski, P. J.; Morley, A.; Muir, K. J. Chem. Soc., Perkin Trans. 1 1999, 955-968. Williams, D. R.; Brooks, D. A.; Berliner, M. A. J. Am. Chem. Soc. 1999, 121, 4924-4925. Williams, D. R. Clark, M. P. Tetrahedron Lett. 1999, 40, 2291-2294. Metternich, R.; Denni, D.; Thai, B.; Sedrani, R. J. Org. Chem. 1999, 64, 9632- 9639.
44. Blakemore, P. R.; Cole, W. J.; Kocienski, P. J.; Morley, A. Synlett 1998, 1, 26-28. For recent applications of this reaction in synthesis, see: Blakemore, P. R.; Kocienski, P. J.; Morley, A.; Muir, K. J. Chem. Soc., Perkin Trans. 1 1999, 955-968. Williams, D. R.; Brooks, D. A.; Berliner, M. A. J. Am. Chem. Soc. 1999, 121, 4924-4925. Williams, D. R. Clark, M. P. Tetrahedron Lett. 1999, 40, 2291-2294. Metternich, R.; Denni, D.; Thai, B.; Sedrani, R. J. Org. Chem. 1999, 64, 9632-9639.
45. This strategy should give us the option to oxidize the C(1) alcohol to acid before coupling with sulfone 7. This route although more convergent, is highly risky. To this end, (-)-61 was converted to iv as outlined below. Unfortunately, coupling with 7 proved impossible; only recovery of sulfone 7 was observed. We reasoned that initial deprotonation of C(2) in iv by the sulfone anion leads to elimination of C(3) methoxy followed by decomposition. To avoid this problem, we introduced the carboxylic acid functionality after union with sulfone 7. matrix presented
46. Protecting group exchange proved very important for the macrolactamization step: unpublished result of Z.W.
47. Crimmins, M. T.; Al-awar, R. S.; Vallin, I. M.; Hollis, W. G., Jr.; O'Mahony, R.; Lever, J. G.; Bankaitis-Davis, D. M. J. Am. Chem. Soc. 1996, 118, 7513-7528.
48. Bald, E.; Saigo, K.; Mukaiyama, T. Chem. Lett. 1975, 1163-1166.