Synthetic studies towards phorboxazole A. Stereoselective synthesis of the C3-C19 bis-oxane oxazole portion of the phorboxazole macrolide

Tetrahedron Letters

Volumn 41, Issue 6, 2000, Pages 983-986

  Pattenden, Gerald ^a   Plowright, Alleyn T ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE; OXAZOLE DERIVATIVE; PHORBOXAZOLE A;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG STRUCTURE; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034607012     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02187-5     Document Type: Article

References (34)

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28. 6, T=340K) δ 4.47-4.39 (1H, m), 4.24 (1H, bd, J∼8.5), 4.19 (1H, bs), 4.13 (1H, ddd, J 10.8, 8.3, 2.0), 4.02-3.93 (1H, m), 3.98 (2H, q, J 7.1), 3.68 (1H, dd, J 8.6, 5.5), 2.51 (1H, dd, J 15.0, 7.3), 2.25 (1H, dd, J 15.0, 6.1), 1.90-1.84 (1H, m), 1.75-1.68 (4H, m), 1.61-1.53 (4H, m), 1.44 (9H, s), 1.30 (1H, ddd, J 13.6, 11.6, 2.5), 1.17-1.03 (21H, m), 1.00 (3H, t).
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31. The vinyl iodide 19 was prepared starting from L-malic acid, based on procedures described earlier, see: Kolb, H. C.; Sharpless, K. B. Tetrahedron 1992, 48, 10515; Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391; Hara, S.; Dojo, H.; Takinami, S.; Suzuki, A. Tetrahedron Lett. 1983, 24, 731.
32. The vinyl iodide 19 was prepared starting from L-malic acid, based on procedures described earlier, see: Kolb, H. C.; Sharpless, K. B. Tetrahedron 1992, 48, 10515; Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391; Hara, S.; Dojo, H.; Takinami, S.; Suzuki, A. Tetrahedron Lett. 1983, 24, 731.
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34. 3) δ 7.57 (1H, d, J 0.8), 7.27 (2H, d, J 8.7), 6.89 (2H, d, J 8.7), 4.91 (1H, dd, J 11.2, 3.2), 4.77 (1H, s), 4.72 (1H, s), 4.56 (2H, s), 4.55 (2H, s), 4.41-139 (1H, m), 4.18-104 (2H, m), 4.01-3.95 (1H, m), 3.81 (3H, s), 3.74-3.71 (2H, m), 2.76 (1H, bs), 2.41 (1H, dd, J 13.2, 4.8), 2.28 (1H, dd, J 13.2, 3.7), 2.08 (1H, bd, J∼14.0), 2.06 (1H, bd, J∼13.2), 1.98-1.80 (4H, m), 1.74-1.70 (2H, m), 1.66-1.60 (2H, m), 1.17-1.04 (21H, m).