中文摘要
Viscolin (1) 係由槲寄生 ( Viscum coloratum ) 中分離所得的1,3-二苯基取代丙烷類化合物。經文獻報導該化合物具抗發炎效果，目前viscolin (1) 全合成之研究僅一篇論文報導且合成步驟冗長。研究者嘗試全新且更有效率之viscolin (1)全合成路徑，以5-溴化香莢蘭醛 (36) 為起始物合成得到苯乙酮類化合物46，接著以該化合物與研究者所合成之香莢蘭醛衍生物48進行醇醛縮合反應 ( Aldol condensation ) 可以得到苯基苯乙醯酮類化合物49，該化合物再經氫化與去保護反應即可成功得到1,3-二苯基取代丙烷類化合物50。以該合成策略期望能藉由較少的合成步驟大量合成出Viscolin (1)，以供藥理活性測試之用。

Abstract
1,3-diphenylpropane, named viscolin (1) , was isolated from Viscum coloratum. In previous report, viscolin (1) exhibited anti-inflammatory activity and only one total synthesis research has been reported with numerous reaction steps. A new and efficient synthetic pathway employed in this work involved Aldol condensation of acetophenones 46 and benzaldehydes 48 , were synthesized from 5-bromovanillin (36) and vanillin (18) . Then, viscolin (1) could be obtained by hydrogenation and deprotection reaction of chalcones 49 , were synthesized. This new strategy describe the development of a short procedure that allows preparation of great amount of viscolin (1) for the research of bioactivity.

1. Leu, Y. L.; Kuo, S. M.,; Hwang, T. L.; Chiu, S. T.; The inhibition of superoxide anion generation by neutrophils from Viscum articulactum. Chem. Pharm. Bull., 2004, 52, 858—860.
2. Leu, Y. L.; Hwang, T. L.; Chung, Y. M.; Hong, P. Y.; The inhibition of superoxide anion generation in human neutrophils by Viscum coloratum. Chem. Pharm. Bull., 2006, 54, 1063—1066
3. Hwang, T. L.; Leu, Y. L.; Kao, S. H.; Tang, M. C.; Chang, H. L.; Viscolin, a new chalcone from Viscum coloratum, inhibits human neutrophil superoxide anion and elastase release via a cAMP-dependent pathway. Free Radical Biol. Med., 2006, 41, 1433–1441.
4. Su, C. R.; Shen, Y.; Chiang.; Kuo, P. C.; Leu, Y. L.; Damu, A. G.; Wang, Y. H.; Wu, T. S.; Total synthesis and biological evaluation of viscolin, a 1,3-diphenylpropane as a novel potent anti-inflammatory agent. Bioorg. Med. Chem. Lett., 2006, 16, 6155–6160.
5. Shriner, R. L.; McCutchan, P.; Preparation of some methylated gallic acids. J. Am. Chem. Soc., 1929, 51 , 2193–2195.
6. Bradley, W.; Robinson, R.; Schwarzenbach, G.; A synthesis of pyrylium salt of delphinidin chloride not involving a demethylation process, and synthesis of hirsutidin chloride and of delphinidin chloride 3’-metthyl ether, possibly identical with petunidin chloride. J. Chem. Soc., London, 1930, 793-811.
7. Wehrli, P. A. (Hofiann-La Roche Inc.).; Process for the preparation of 2,4,5-trimethoxybenzaldehyde. Chem. Abstr., 1974, 80, 1474lf.
8. Ellis, J. E.; Lenger,S. R.; A convenient synthesis of 3,4-dimethoxy-5-hydroxybenzaldehyde. Synth. Commun., 1998, 28, 1517-1524.
9. Tummatorn, J.; Khorphueng, P.; Petsom, A.; Muangsin, N.; Chaichit, N.; Roengsumran, S.; Convenient synthetic route to a dehydrorotenoid via selective intramolecular aldol condensation of 1,2-diaryl diketone. Tetrahedron, 2007, 63, 11878–11885.
10. Bao, K.; Fan, A.; Dai, Y.; Zhang, L.; Zhang, W.; Cheng, M.; Yao, X.; Selective demethylation and debenzylation of aryl ethers by magnesium iodide under solvent-free conditions and its application to the total synthesis of natural products. Org. Biomol. Chem., 2009, 7, 5084–5090.
11. Alves, A. P. L.; Jünior, J. B. C.; Slana, G. B. A.; Cardoso, J. N.; Wang, Q.; Lopes, R. S. C.; Lopes, C. C.; Synthesis of 1,2,4-Trimethoxybenzene and Its Selective Functionalization at C-3 by Directed Metalation. Synth. Commun., 2009, 39, 3693-3790.
12. Nolasco, L.; Gonzalez, M. P.; Caggiano, L.; Jackson, R. F. W.; Application of negishi cross-coupling to the synthesis of the cyclic tripeptides of 4949-III and K-13. J. Org. Chem., 2009, 74, 8280–8289.
13. TöKẻs, A. T.; Synthesis of 8-Chloro-3’,4’,5’,7’-tetrahydroxyiosflavone possessing antioxidant activity. J. Antibiot., 1990, 43, 1332-1333
14. Combes, S.; Finet, J.-P.; Siri, D.; On the optical activity of the 3-aryl-4- hydroxycoumarin isolated from Millettia griffoniana: molecular modelling and total synthesis. J. Chem. Soc., Perkin Trans. 1, 2002, 38–44
15. Manfroni, G.; Gatto, B.; Tabarrini, O,; Sabatini, S,; Cecchetti, V.; Giaretta, G,; Parolin, C,; Vecchio, C. D.; Calistri, A.; Palumbo, M.; Fravolini, A.; Synthesis and biological evaluation of 2-phenylquinolones targeted at Tat/TAR recognition. Bioorg. Med. Chem. Lett., 2009, 19, 714–717
16. Katritzky, A. R.; Long, Q.; He, H.-Y.; Qina, G.; Wilcox, A. L.; Preparation of 2-alkoxy-5-methoxybenzaldehydes and 2-ethoxy-5-alkoxybenzaldehydes. Arkivoc, 2000, 6, 868-875.
17. Getahun, Z.; Jurd, L.; Chu, P. S.; Lin, C. M.; Hamel, E.; Synthesis of alkoxy-substituted diary1 compounds and correlation of ring separation with inhibition of tubulin polymerization: differential enhancement of inhibitory effects under suboptimal polymerization reaction conditions. J. Med. Chem., 1992, 35, 1058-1067
18. Alvarez, S.; Alvarez, R.; Khanwalkar, H.; Germain, P.; Lemaire, G.; Rodriguez-Barrios, F.; Gronemeyer, H.; de Lera, A. R.; Retinoid receptor subtype-selective modulators through synthetic modifications of RARc agonists. Bioorg. Med. Chem. Lett., 2009, 17, 4345–4359
19. Andries, V.; Depreux, P.; Synthesis of a fluorescent naphthalenic ligand of melatonin receptors. Synth. Commun., 1997, 27, 4207-4214
20. Ploypradith, P.; Cheryklin, P.; Niyomtham, N.; Bertoni, D. R.; Ruchirawat, S.; Solid-supported acids as mild and versatile reagents for the deprotection of aromatic ethers. Org. Lett., 2007, 9 , 2637–2640
21. Gutsche, C. D.; Jason, E. F.; Coffey, R. S.; Johnson, H. E.; Experiments in the colchicine field. V. the thermal and photochemical decomposition of various 2- (β-phenylethy1)-phenyldiazomethanes and 2- (7-phenylpropyl)- phenyldiazomethanesl. J. Am. Chem. Soc., 1958, 80, 5756–5767
22. Paulo A. de Almeidaa, Silas V. Fraiz Jr.a, Raimundo Braz-Filhob; Synthesis and Structural Confirmation of Natural 1,3-Diarylpropanes. J. Braz. Chem. Soc., 1999, 10, 347-353.
23. Kursanov, D. N.; Parnes, Z. N.; Bassova, G. I. ; Loim, N. M.; Zdanovich, V. I. Ionic hydrogenation of the ethylene Bond and the double bond of the carbonyl group. Tetrahedron, 1967 ,23 , 2235-2242
24. Simons, L. J.; Caprathe, B. L.; Callahan, M.; Graham, J. M.; Kimura, T.; Lai, Y.; LeVine III, H.; Lipinski, W.; Sakkab, A. T.; Tasaki, Y,; Walker a, L. C. Yasunaga, T.; Ye, Y.; Zhuang, N.; Augelli-Szafran, C. E.; The synthesis and structure–activity relationship of substituted N-phenyl anthranilic acid analogs as amyloid aggregation inhibitors. Bioorg. Med. Chem. Lett., 2009, 19, 654–657
25. Pashkovskii, F. S. ; Shchukina, E. M.; Gribovskii, M. G.; Lakhvich, F. A.; Heterocyclic analogs of prostaglandines: iv. synthesis of 3,7-interphenylene 3,10(11)-dioxa-13-azaprostanoids and 9-oxa-7-azaprostanoids based on tetronic acid and aromatic aldehydes. Russ. J. Org. Chem., 2008, 44, 657-670
26. Morgan, B. J.; Mulrooney, C. A.; Kozlowski, M. C.; Perylenequinone natural products: evolution of the total synthesis of cercosporin. J. Org. Chem., 2010, 75, 44–56
27. Sala, T.; Sargent, M. V.; Depsidone synthesis. part 14.1 the total synthesis of psoromic acid : lsopropyl ethers as useful phenolic protective groups. J. Chem. Soc. Perkin Trans. 1, 1979, 2593 – 2598
28. Ohta, T.; Fukuda, T.; Ishibashi, F.; Iwao, M.; Design and synthesis of lamellarin D analogues targeting topoisomerase I. J. Org. Chem., 2009, 74, 8143–8153