Synthesis of both enantiomers of the BC-ring part of ciguatoxin

Tetrahedron

Volumn 52, Issue 37, 1996, Pages 12091-12110

  Oka, Takahiro ^a   Fujiwara, Kenshu ^a   Murai, Akio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CIGUATOXIN;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030576873     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00700-4     Document Type: Article

References (40)

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28. 8. Epoxidation of 9 with mCPBA gave 10 in 86% yield, along with β-epoxide in 10% yield.
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31. 1H NMR (270MHz) of 12: δ 7.35-7.21 (7H, m), 6.85 (2H, d, J = 9 Hz), 5.91 (1H, ddd, J = 7, 10, 17 Hz, H-8), 5.38 (1H, dd, J = 2, 9 Hz, H-3), 5.29 (1H, br d, J = 17 Hz, H-9-trans), 5.14 (1H, br d, J = 10 Hz, H-9-cis), 5.04 (1H, d, J = 2 Hz, H-6), 4.79 (1H, d, J = 11 Hz), 4.65 (1H, d, J = 11 Hz), 4.61 (1H, d, J = 11 Hz), 4.42(1H, d, J =11 Hz), 4.22 (1H, br d, J = 7 Hz, H-7), 4.19 (1H, dd, J = 3, 9Hz, H-4), 3.93-3.89 (1H, m, H-2), 3.80 (3H, s), 3.78 (1H, d, J = 3 Hz, H-5), 3.72 (1H, dd, J = 4, 10 Hz, H-1), 3.57 (1H, dd, J = 8, 10 Hz, H-1), 2.12 (3H, s), 1.85 (3H, s), 0.88 (9H, s), 0.034 (3H, s), and 0.029 (3H, s).
32. 1H NMR (270 MHz) of peracetylated compound of 20: δ 7.40-7.26 (5H, m), 6.78 (2H, d, J = 4, 16 Hz, H-3), 6.04 (1H, br d, J = 16 Hz, H-2), 5.44 (1H, br d, J = 7 Hz, H-9), 4.86 (1H, d, J = 12 Hz), 4.72 (1H, d, J = 12 Hz), 4.29 (1H, dd, J = 3, 10Hz, H-10), 4.20 (2H, q, J = 7 Hz), 4.11 (1H, dd, J = 8, 10 Hz, H-10), 4.02 (1H, br d, J = 3 Hz, H-4), 3.88 (1H, br s, H-5), 3.76 (1H, t, J = 9 Hz, H-7), 3.70 (1H, dd, J = 2, 9 Hz, H-6), 3.52 (1H, br d, J = 9 Hz, H-8), 2.07 (3H, s), 2.00 (3H, s), 1.28 (3H, t, J = 7 Hz), 0.95 (9H, s), 0.89 (3H, s), 0.19 (3H, s), 0.112 (3H, s), 0.107 (3H, s), and 0.01 (3H, s).
33. 1H NMR (400 MHz) of peracetylated compound of 23: δ 7.33 (2H, d, J = 9 Hz), 6.86 (2H, d, J = 9 Hz), 5.76 (1H, br dt, J = 16,4 Hz, H-2), 5.66 (1H, br dd, J = 5, 16 Hz, H-3), 5.41 (1H, ddd, J = 1,3, 8 Hz, H-9), 4.78 (1H, d, J = 11 Hz), 4.64 (1H, d, J = 11 Hz), 4.21-4.08 (4H, m, H-1 and 10), 3.82 (1H, br d, J = 5 Hz, H-4), 3.78 (3H, s), 3.75 (1H, d, J = 2 Hz, H-5), 3.70 (1H, t, J = 9 Hz, H-7), 3.66 (1H, dd, J = 2, 9 Hz, H-6), 3.44 (1H, dd, J = 1, 9 Hz, H-8), 2.06 (3H, s), 1.98 (3H, s), 0.96 (9H, s), 0.92 (9H, s), 0.90 (9H, s), 0.18 (3H, s), 0.13 (3H, s), 0.11 (3H, s), 0.06 (6H, s), and 0.03 (3H, s).
34. 14. a) Johnston, B. D.; Oehlschlarer, A. C. J. Org. Chem. 1982, 47, 5384.
35. b) Pridgen, L. N.; Schilcrat, S. C.; Lantos, I. Tetrahedron Lett. 1984, 25, 2835.
36. 1H NMR (400 MHz) of peracetylated compound of 28: δ 7.32-7.24 (5H, m), 7.16 (2H, d, J = 9 Hz), 6.84 (2H, d, J = 9 Hz), 5.90 (1H, dd, J = 8, 16 Hz, H-9), 5.79 (1H, dt, J = 16, 5 Hz, H-10), 5.77 (1H, ddd, J = 7, 10, 16Hz, H-2), 5.32 (1H, t, J = 10 Hz, H-6), 5.27 (1H, br d, J= 16Hz, H-1-trans), 5.21 (1H, br d, J = 10 Hz, H-1-cis), 4.97 (1H, t, J = 10 Hz, H-4), 4.62 (2H, br d, J = 5 Hz, H-11), 4.55 (1H, d, J = 11 Hz), 4.54 (1H, d, J = 11 Hz), 4.49 (1H, d, J = 11 Hz), 4.28 (1H, d, J = 11 Hz), 3.84 (1H, dd, J = 3, 8 Hz, H-8), 3.79 (3H, s), 3.68 (1H, dd, J = 7, 10 Hz, H-3), 3.67 (1H, t, J = 10 Hz, H-5), 3.48 (1H, dd, J = 3, 10 Hz, H-7), 2.10 (3H, s), 1.96 (3H, s), and 1.80 (3H, s).
37. 1H NMR (400 MHz) of peracetylated compound of 30: δ 7.40-7.25 (5H, m), 7.17 (2H, d, J = 9 Hz), 6.85 (2H, d, J = 9 Hz), 5.90 (1H, br dd, J = 9, 18 Hz, H-9), 5.75 (1H, dt, J = 18, 6 Hz, H-10), 5.80-5.69 (1H, m, H-2), 5.41 (1H, t, J = 8 Hz, H-6), 5.37-5.22 (2H, m, H-1), 5.30 (1H, t, J = 4 Hz, H-4), 4.61 (2H, br d, J= 5 Hz, H-11), 4.58 (1H, d, J = 12 Hz), 4.54 (1H, d, J = 12 Hz), 4.55-4.48 (1H, m, H-3), 4.37 (1H, d, J = 12 Hz), 4.32 (1H, d, J = 12 Hz), 3.94 (1H, dd, J = 5, 9 Hz, H-8), 3.80 (3H, s), 3.69 (1H, dd, J = 5, 8 Hz, H-7), 3.63 (1H, dd, J = 4, 8 Hz, H-5), 2.11 (3H, s), 2.09 (3H, s), and 1.91 (3H, s).
38. 1H NMR (400 MHz) of peracetylated compound of 31: δ 7.38-7.22 (5H, m), 7.15 (2H, d, J = 9 Hz), 6.83 (2H, d, J = 9 Hz), 6.01 (1H, br dt, J = 18, 11 Hz, H-2), 5.83 (1H, br dt, J = 16, 6 Hz, H-10), 5.56 (1H, br dd, J = 8, 16 Hz, H-9), 5.30 (1H, t, J = 6 Hz, H-4), 5.15 (1H, br d, J = 11 Hz, H-1-cis), 5.14 (1H, br d, J = 18 Hz, H-1-trans), 4.95 (2H, br d, J = 4 Hz, H-11), 4.93 (1H, dd, J = 4, 8 Hz, H-7), 4.57 (1H, d, J = 12 Hz), 4.55 (1H, d, J =12 Hz), 4.53 (1H, d, J = 12 Hz), 4.38 (1H, d, J = 12 Hz), 4.18 (1H, dd, J = 5, 8 Hz, H-6), 4.12 (1H, br dd, J = 4, 8 Hz, H-8), 3.96 (1H, dd, J = 5, 6 Hz, H-5), 3.76 (3H, s), 3.67 (1H, dd, J = 6, 11 Hz, H-3), 2.07 (3H, s), 2.05 (3H, s), and 2.00 (3H, s).
39. 1H NMR (400 MHz) of peracetylated compound of 32: δ 7.38-7.18 (7H, m), 6.86 (2H, d, J = 9 Hz), 5.92-5.72 (2H, m, H-2, and 10), 5.62 (1H, br dd, J = 6, 18 Hz, H-9), 5.40 (1H, dd, J = 2, 11 Hz, H-3), 5.31 (1H, br d, J = 18 Hz, H-1-trans), 5.18 (1H, br d, J = 11 Hz, H-1-cis), 5.04 (1H, dd, J = 5, 8 Hz, H-6), 4.62 (1H, d, J = 12 Hz), 4.58-4.48 (4H, m, H-4, 7, and 11), 4.45 (1H, d, J = 12 Hz), 4.38 (1H, d, J = 12 Hz), 4.33 (1H, d, J = 12 Hz), 4.31 (1H, br d, J = 6 Hz, H-8), 4.19 (1H, t, J = 5 Hz, H-5), 2.09 (3H, s), 2.06 (3H, s), and 1.90 (3H, s).
40. 17. Barton, D. H. R.; McCombie, S. W.; J. Chem. Soc., Perkin Trans. 1 1975, 61, 313.