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Synlett

Volumn , Issue 12, 2008, Pages 1801-1804

Total synthesis of (S)-(-)-curvularin: A ring-closing-metathesis-based construction of the macrocyclic framework

(4) Mohapatra, Debendra K a Rahaman, Hasibur a Pal, Rita a Gurjar, Mukund K a

a NATIONAL CHEMICAL LABORATORY (India)

Author keywords

Curvularin; Cytotoxic; Pinnick oxidation; Ring closing metathesis; Wittig reaction

Indexed keywords

CURVULARIN; PLANT TOXIN;

ARTICLE; CHEMICAL STRUCTURE; OXIDATION; RING CLOSING METATHESIS; SYNTHESIS; WITTIG REACTION;

EID: 48349145274 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078504 Document Type: Article

Times cited : (21)

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28
- 48349128700
- Analytical and Spectral Data of 10 IR (neat, 3032, 2933, 1673, 1598, 1572, 1513, 1436, 1384, 1320, 1247, 1152, 1090, 1031, 820, 754, 698 cm-1. 1H NMR (200 MHz, CDCl3, δ, 3.21 (t, J, 6.6 Hz, 2 H, 3.59 (t, J, 6.6 Hz, 2 H, 3.67 (s, 3 H, 4.35 (s, 2 H, 4.95 (s, 2 H, 4.99 (s, 2 H, 6.40 (d, J, 2.2 Hz, 1 H, 6.42 (d, J, 2.2 Hz, 1 H, 6.73 (d, J, 8.6 Hz, 2 H, 7.12 (d, J, 8.7 Hz, 2 H, 7.22-7.32 (m, 10 H, 10.45 (s, 1 H) ppm. 13C NMR 50 MHz, CDCl3, δ, 34.9, 55.2, 70.1, 70.2, 70.6, 72.3, 98.4, 110.1, 113.6, 117.4, 127.3, 127.6, 128.2, 128.3, 128.7, 129.2, 130.7, 135.9, 135.9, 145.3, 159.0, 163.4, 164.4, 190.3 ppm. Anal. Calcd for C 31H30O5: C, 77.16; H, 6.27. Found: C, 77.46; H, 6.21
- 5: C, 77.16; H, 6.27. Found: C, 77.46; H, 6.21.

29
- 48349086425
- Analytical and Spectral Data of 11 IR (neat, 3400, 2930, 1600, 1512, 1454, 1383, 1302, 1247, 1151, 1084, 1030, 822, 738, 698 cm-1. 1H NMR (200 MHz, CDCl3, δ, 2.42-2.55 (m, 1 H, 2.64-2.79 (m, 1 H, 2.84-3.03 (m, 2 H, 3.51-3.67 (m, 2 H, 3.77 (s, 3 H, 4.39 (d, J, 11.5 Hz, 1 H, 4.45 (d, J, 11.6 Hz, 1 H, 4.85-4.95 (m, 2 H, 4.97 (s, 2 H, 5.01-5.02 (m, 1 H, 5.05 (s, 2 H, 5.66-5.87 (m, 1 H, 6.42 (d, J, 2.4 Hz, 1 H, 6.51 (d, J, 2.4 Hz, 1 H, 6.83 (d, J, 8.5 Hz, 2 H, 7.20 (d, J, 8.5 Hz, 2 H, 7.33-7.41 (m, 10 H) ppm. 13C NMR 50 MHz, CDCl3, δ 34.6, 55.2, 70.0, 70.1, 70.4, 72.6, 99.2, 108.2, 113.7, 114.3, 116.0, 118.7, 126.3, 126.9, 127.2, 127.6, 127.8, 128.0, 128.5, 128.6, 129.3, 130.4, 132.0, 134.0, 136.7, 136.8, 138.9, 139.3, 158.1, 158.3, 159.1. Anal. Calcd for C34H36O 5: C, 77.84; H, 6.92. Found: C, 77.69; H, 6.82
- 5: C, 77.84; H, 6.92. Found: C, 77.69; H, 6.82.

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33
- 48349121467
- Analytical and Spectral Data of 6 IR (neat, 3065, 3031, 2927, 2855, 1730, 1602, 1454, 1385, 1254, 1105, 836, 756, 616 cm-1. 1H NMR (200 MHz, CDCl3, δ, 0.11 (s, 3 H, 0.05 (s, 3 H, 0.88 (s, 9 H, 2.40-2.54 (m, 1 H, 2.61-2.75 (m, 1 H, 3.96 (d, J, 16.7Hz, 1 H, 4.45 (d, J, 16.7 Hz, 1 H, 4.97-5.08 (m, 6 H, 5.55-5.58 (m, 1 H, 5.68-5.89 (m, 1 H, 6.52-6.60 (m, 2 H, 7.30-7.48 (m, 10 H) ppm. 13C NMR 50 MHz, CDCl3, δ, 3.7, 17.9, 25.6, 34.8, 40.2, 70.0, 70.2, 77.5, 99.1, 104.2, 114.3, 114.7, 119.3, 126.9, 127.1, 127.5, 127.7, 127.8, 127.9, 128.0, 128.1, 128.2, 128.4, 128.5, 128.6, 131.8, 132.4, 136.2, 136.3, 136.6, 136.9, 141.7, 154.9, 159.8, 170.4 ppm. Anal. Calcd for C32H40O5Si: C, 72.14; H, 7.57. Found: C, 72.31; H, 7.39
- 5Si: C, 72.14; H, 7.57. Found: C, 72.31; H, 7.39.

34
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35
- 48349138561
- 12O: C, 71.95; H, 12.08. Found: C, 71.89; H, 12.11.
- 12O: C, 71.95; H, 12.08. Found: C, 71.89; H, 12.11.

36
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37
- 48349088165
- Analytical and Spectral Data of 4 [α]D 25 +7.86 (c 1.5, CHCl3, IR (neat, 2929, 2371, 2361, 2341, 1730, 1604, 1383, 1257, 1146, 1068, 773, 696, 667 cm-1. 1H NMR (200 MHz, CDCl3, δ, 0.16 (s, 3 H, 0.01 (s, 3 H, 0.86 (s, 9 H, 1.22 (d, J, 5.7 Hz, 1.5 H, 1.25 (d, J, 5.7 Hz, 1.5 H, 1.47-1.79 (m, 2 H, 1.99-2.16 (m, 2 H, 2.37-2.50 (m, 1 H, 2.61-2.75 (m, 1 H, 3.70-3.88 (m, 1 H, 4.37-4.50 (m, 1 H, 4.92-5.07 (m, 9 H, 5.50-5.56 (m, 1 H, 5.67-5.91 (m, 2 H, 6.48 (d, J, 2.3 Hz, 1 H, 6.53 (br s, 1 H, 7.31-7.42 (m, 10 H) ppm. 13C NMR 50 MHz, CDCl 3, δ, 5.2,-4.9, 18.2, 19.9, 20.0, 25.9, 29.6, 29.7, 35.1, 69.9, 70.2, 70.5, 70.6, 98.9, 108.5, 108.6, 115.0, 116.4, 124.2, 126.9, 127.2, 127.5, 127.7, 128.0, 128.4, 128.5, 128.6, 135.9, 136.8, 137.0, 137.7, 158.2, 158.3, 170.9, 171.9 ppm. Anal. Calcd for C38H50O 5Si: C
- 5Si: C, 74.23; H, 8.20. Found: C, 74.01; H, 8.22.

38
- 33746238145
- For general reviews on RCM, see: a
- For general reviews on RCM, see: (a) Grubbs, R. H. Angew. Chem. Int. Ed. 2006, 45, 3760.
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- Grubbs, R.H.¹

39
- 33751203394
- (b) Chauvin, Y. Angew. Chem. Int. Ed. 2006, 45, 3741.
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- Chauvin, Y.¹

40
- 33746238148
- (c) Schrock, R. R. Angew. Chem. Int. Ed. 2006, 45, 3748.
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41
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- Fürstner, A.¹ Müller, C.²

42
- 2942589152
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43
- 0001399412
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44
- 0032580376
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45
- 0030857814
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46
- 48349119515
- Analytical and Spectral Data of 16 [α]D 25 +45.05 (c 1.0, CHCl3, IR (neat, 3208, 2928, 1728, 1687, 1655, 1601, 1429, 1311, 1154, 1105, 754 cm-1. 1H NMR (200 MHz, CDCl3, δ, 1.09 (d, J, 6.3 Hz, 3 H, 1.47-1.62 (m, 2 H, 1.91-1.99 (m, 1 H, 2.14-2.26 (m, 1 H, 3.05-3.55 (m, 4 H, 4.94-5.02 (m, 5 H, 5.15-5.25 (m, 1 H, 5.38-5.51 (m, 1 H, 6.46 (d, J, 2.1 Hz, 1 H, 6.52 (s, 1 H, 7.22-7.36 (m, 10 H) ppm. 13C NMR 50 MHz, CDCl3, δ, 20.9, 30.4, 33.7, 38.0, 49.0, 70.2, 70.6, 72.4, 99.6, 109.5, 120.1, 124.3, 127.2, 127.6, 128.0, 128.1, 128.6, 134.1, 136.2, 136.5, 137.2, 156.6, 160.2, 170.8, 204.6 ppm. Anal. Calcd for C 30H30O5: C, 76.57; H, 6.43. Found: C, 76.42; H, 6.49
- 5: C, 76.57; H, 6.43. Found: C, 76.42; H, 6.49.

47
- 48349089232
- Analytical and Spectral Data of 1 [α]D 25 -31.89 (c 2.0, EtOH, lit14 [α] D25 -33.0 (c 2.0, EtOH, IR (Nujol, 3419, 3176, 2933, 2869, 2254, 1719, 1661, 1607, 1589, 1463, 1316, 1264, 1105, 1006, 823, 616. cm-1. 1H NMR (500 MHz, acetone-d 6, δ, 1.13 (d, J, 6.3 Hz, 3 H, 1.24-1.28 (m, 2 H, 1.40-1.50 (m, 3 H, 1.52-1.57 (m, 1 H, 1.59-1.64 (m, 1 H, 1.73-1.80 (m, 1 H, 2.78 (ddd, J, 2.9, 9.8, 15.5 Hz, 1 H, 3.12 (ddd, J, 2.9, 8.7, 15.5 Hz, 1 H, 3.71 (d, J, 15.7 Hz, 1 H, 3.79 (d, J, 15.6 Hz, 1 H, 4.90-4.96 (m, 1 H, 6.36 (d, J, 2.2 Hz, 1 H, 6.41 (d, J, 2.2 Hz, 1 H, 8.82 (br s, 1 H, 9.19 (br s, 1 H) ppm. 13C NMR 50 MHz, acetone-d6, δ, 20.5, 23.4, 24.5, 27.4, 32.8, 39.6, 44.0, 72.6, 102.4, 112.2, 121.3, 136.9, 158.2, 160.1, 171.0, 206.7 ppm. Anal. Calcd for
- 5: C, 65.74; H, 6.90. Found: C, 65.68; H, 6.91.

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