1492 (w), 1437 (s), 1386 (s), 1354 (m), 1319 (s),1230 (s), 1198 (m),. 1142 (s), 1014 (m), 776 (m), 767 (m), 702 (s); cm−1; GC-MS (EI, 70 eV): m/z (%): 288 (M + , 100), 245 (9), 244 (38), 216 (11), 215 (54), 213 (8), 202 (3), 189 (3), 152 (5), 139 (3), 122 (6), 113 (4), 107 (16), 94 (7). HRMS (EI): calcd for C20H16O2 [M + ]: 288.10632, found 288.105768. Me OH O 5'-Hydroxy-6'-methyl-[1,1';3',1'']terphenyl-4'-carboxylic acid methyl ester (17c); Starting with 15 (453mg, 1.65 mmol), 16c ( 444mg, 1.5 mmol), TiCl4 (0.2ml, 1.65 mmol) and CH2Cl2 (9ml), 17c was isolated as a gummy compound (222.9mg, 37%); 1 H NMR (300 MHz, CDCl3): δ = 2.12 (s, 3H, CH3), 3.39 (s, 3H, OCH3), 6.66-7.29 (m, 11H, ArH), 11.05 (s, 1H, OH); 13 C NMR (75 MHz, CDCl3): δ = 13.7 (CH3), 52.1 (OCH3), 110.4, 123.7, 124.2, 127.1, 127.6 (ArCH), 127.9, 128.0, 128.5 (2C ArCH), 141.2, 141.9, 143.3, 145.3, 144.5, 147.5, 160.6 (ArCH), 172.3 (C); IR (neat): ν̃ = 3426 (m), 3087 (w), 3052 (m), 3028 (m), 2947 (m), 1664 (s), 1597 (m), 1556 (m), 1493 (w), 1437 (s), 1386 (s), 1359 (m), 1320 (s), 1256 (s), 1230 (s), 1198 (m),. 1143 (s), 1014 (m), 776 (m), 767 (m), 702 (s); cm−1; GC-MS (EI, 70 eV): m/z (%):318 (M+, 100), 300 (20), 288 (4), 276 (3), 245 (9), 244 (38), 216 (11), 215 (54), 213 (8), 202 (9), 189 (7), 152 (3), 139 (9), 122 (8), 113 (6), 107 (16), 94 (7). HRMS (EI): calcd for C21H18O3 [M + ]: 318.10654, found 318.109762. OMe 90
Refrences 1. Handbook <strong>of</strong> Chemistry and Physics, 81st Edition CRC Press ISBN 0-8493- 0481-4. 2. Cavallito, C. J.; Bailey, J. H. J. Am. Chem. Soc., 1944, 66, 1950. 3. http://www.phytochemicals.info/phytochemicals/allicin.php 4. Fleischauer, A. T.; Arab L. J. Nutr. 2001, 131, 1032. 5. Herman-Antosiewicz, A.; Singh, S. V. Mutat. Res 2004, 555, 121. 6. Milner, J. A. J Nutr 2001, 131, 1027. 7. Pinto, J. T.; Lapsia, S.; Shah, A.; Santiago, H.; Kim, G. Antiproliferative effects <strong>of</strong> garlic-derived and other allium related compounds. In: Go VLW, editor. Nutrition and cancer prevention: new insights into the role <strong>of</strong> phytochemicals. Advances in experimental medicine and biology, 492, chapter 8. New York: Kluwer Academic/Plenum Publishers; 2001. p. 83–106. 8. Wu, X.; Kassie, F.; Mersch-Sundermann, V. Mutat. Res. 2005, 589, 81. 9. See for example: Mori, Y.; Taneda, S.; Hayashi, H.; Sakushima, A.; Kamata, K.; Suzuki, A. K.; Yoshino, S.; Sakata, M.; Sagai, M.; Seki, K.-i. Biol. Pharm. Bull. 2002, 25, 145. 10. (a) Davidson, B. S.; Molinski, T. F.; Barrows, L. R.; Ireland, C. M. J. Am. Chem. Soc. 1991, 113, 4709. (b) Behar, V.; Danishefsky, S. J. J. Am. Chem. Soc. 1993, 115, 7017. (c) Toste, F. D.; Still, I. W. J. J. Am. Chem. Soc. 1995, 117, 7261. 91
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Synthesis of functionalized 2-(aryl
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The ink of the scholar is more holy
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Affectionately Dedicated to “All
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Table of Contents 03 List of used a
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RCM Ring Closing Metathesis TBAI Te
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humans: 1) the thiomethyl of methio
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Chart 3. Structure of sumatriptan S
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disulfide (DADS) and diallyl sulfid
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1. Synthesis of functionalized 2-(a
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3-Arylthio-1-trimethylsilyloxy-1,3-
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under kinetic reaction control, by
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l a u 4-FC6H4 H Me H 40 m a v 4-FC6
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Table 2. Synthesis of thioxanthones
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3a O OSiMe 3 O OMe + Me Me Cl 3TiO
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Table 3. Synthesis of 8a-x 3 7 8 Ar
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Cl + SPh OSiMe 3 3a 9 O OMe O O H i
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solution. The use of an excess (1.5
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Table 4. Synthesis of 12a-r 3 11 12
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2.3 Conclusion In conclusion, I hav
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aromatization). An unseparable 1:2
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Table 5. Synthesis of arenes 14a-l
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