海洋天然产物Urceolatin的全合成研究
|
摘要
本论文的研究目标是采用汇聚合成策略,为海洋天然产物Urceolatin(P1)设计合成路线。工作重点开展于海洋天然产物Urceolatin(P1)的重要中间体1,2-二苯乙烯衍生物的合成研究和通过光环化反应制取菲并[4,5-bcd]呋喃结构分子前体的研究上,包括两章内容：
第一章海洋天然产物Urceolatin(P1)的全合成研究
本章通过对海洋天然产物Urceolatin(P1)生源合成路线的模拟,设计了针对三个片段分子依次进行偶联的汇聚合成路线。三个片段分子合成路线为：从简单易得的对羟基苯甲醛开始,完成了对芳醛片段分子的多步合成；以没食子酸为起点,构筑出了所需的溴瓮盐片段分子；以原儿茶醛为初始原料合成出了格氏试剂片段分子。再进行两次关键连片：通过关键反应Wittig反应将芳醛片段分子与溴瓮盐片段分子进行偶联,制得了二苯基乙烯衍生物,再经过光环化反应,得到了菲并[4,5-bcd]呋喃结构分子的前体,即多溴代多酚的菲结构类化合物；紧接着对该化合物分子完成呋喃成环化反应后,将得到的菲并[4,5-bcd]呋喃结构分子(P1的重要亚结构)与格氏试剂片段分子再进行对接,可得到Urceolatin(P1)的最终基本骨架,此研究正在进行中。该汇聚合成路线总共经历十九步,目前完成了前十二步,已经制得了相应的芳醛片段分子系列,溴瓮盐片段分子系列,多溴代多酚的菲结构类化合物分子,以及格氏试剂片段分子的前体,涉及了三十九个化合物的合成与表征,包括六个新化合物并得到了相应的波谱数据。
第二章Urceolatin(P1)关键中间体二苯乙烯衍生物的合成研究
本章首先简要综述了二苯乙烯衍生物的合成方法,选用了Wittig反应作为关键连片反应的策略,然后对其进行了较为系统的研究,具体包括：对Wittig反应的前体化合物的筛选(改进了底物的合成路线)；反应条件的优化(试验了多组条件后提高了反应产率)。最后选定了具体Wittig反应前体及其合成路线,并且合成了多种芳醛分子和一系列溴瓮盐分子,以及不对称1,2-二苯基乙烯衍生物系列(光环化反应的前体化合物),为之后进行的光环化反应研究提供了多种底物。
This thesis aims at the studies on design of the total synthetic route of Urceolatin (P1), a component from a marine algae extract, including the study on the synthesis of the asymmetric stilbenes, which are key intermediates of P1, and the study on the photocyclization reaction to yeild the precursor of phenanthro[4,5-bcd]furan structured molecules. This thesis consists of the following two chapters:
Chapter 1. Studies on the Total Synthesis of Urceolatin By imitating the biogenetic route of P1, a convergent synthetic route has been designed. The details of the route are as follows:From commercially available reangents p-hydroxyphenylaldehyde, Protocatechuic aldehyde, and Gallic acid, to produce three key segments respectively. Then by Wittig reaction of two segments of the three (aldehyde segment and Wittig reangent segment) to yeild a series of asymmetric stilbenes, which is under irradiation to yeild the phenanthrene derivatives, as a key precursor of phenanthro[4,5-bcd]furan structure, then by furan ring-closing reaction and Grignard reaction with the last segment (Grignard reangent segment) to synthesize the final product P1, the above mentioned work is ongoing till now. We have completed 12 steps of the synthesis(The total synthetic route is constitueted by 19 steps), including Wittig reaction, photocyclization reaction(two key steps). And 39 compounds, among which 6 are new ones, have been synthesized with reletive spectra data.
Chapter 2. Studies on the Stilbenes Derivatives as Key Intermediates of P1 With the brief review of the methods for making stilbenes, Wittig reaction has been chosen as the key coupling step finally. And a systematic study has been taken on this step. By the experiments results of Wittig reactions, an optimalized route and proper conditions have been decided, then a series of stilbenes have been made, which are precursor of the photocyclization reaction.
第一章海洋天然产物Urceolatin(P1)的全合成研究
本章通过对海洋天然产物Urceolatin(P1)生源合成路线的模拟,设计了针对三个片段分子依次进行偶联的汇聚合成路线。三个片段分子合成路线为：从简单易得的对羟基苯甲醛开始,完成了对芳醛片段分子的多步合成；以没食子酸为起点,构筑出了所需的溴瓮盐片段分子；以原儿茶醛为初始原料合成出了格氏试剂片段分子。再进行两次关键连片：通过关键反应Wittig反应将芳醛片段分子与溴瓮盐片段分子进行偶联,制得了二苯基乙烯衍生物,再经过光环化反应,得到了菲并[4,5-bcd]呋喃结构分子的前体,即多溴代多酚的菲结构类化合物；紧接着对该化合物分子完成呋喃成环化反应后,将得到的菲并[4,5-bcd]呋喃结构分子(P1的重要亚结构)与格氏试剂片段分子再进行对接,可得到Urceolatin(P1)的最终基本骨架,此研究正在进行中。该汇聚合成路线总共经历十九步,目前完成了前十二步,已经制得了相应的芳醛片段分子系列,溴瓮盐片段分子系列,多溴代多酚的菲结构类化合物分子,以及格氏试剂片段分子的前体,涉及了三十九个化合物的合成与表征,包括六个新化合物并得到了相应的波谱数据。
第二章Urceolatin(P1)关键中间体二苯乙烯衍生物的合成研究
本章首先简要综述了二苯乙烯衍生物的合成方法,选用了Wittig反应作为关键连片反应的策略,然后对其进行了较为系统的研究,具体包括：对Wittig反应的前体化合物的筛选(改进了底物的合成路线)；反应条件的优化(试验了多组条件后提高了反应产率)。最后选定了具体Wittig反应前体及其合成路线,并且合成了多种芳醛分子和一系列溴瓮盐分子,以及不对称1,2-二苯基乙烯衍生物系列(光环化反应的前体化合物),为之后进行的光环化反应研究提供了多种底物。
This thesis aims at the studies on design of the total synthetic route of Urceolatin (P1), a component from a marine algae extract, including the study on the synthesis of the asymmetric stilbenes, which are key intermediates of P1, and the study on the photocyclization reaction to yeild the precursor of phenanthro[4,5-bcd]furan structured molecules. This thesis consists of the following two chapters:
Chapter 1. Studies on the Total Synthesis of Urceolatin By imitating the biogenetic route of P1, a convergent synthetic route has been designed. The details of the route are as follows:From commercially available reangents p-hydroxyphenylaldehyde, Protocatechuic aldehyde, and Gallic acid, to produce three key segments respectively. Then by Wittig reaction of two segments of the three (aldehyde segment and Wittig reangent segment) to yeild a series of asymmetric stilbenes, which is under irradiation to yeild the phenanthrene derivatives, as a key precursor of phenanthro[4,5-bcd]furan structure, then by furan ring-closing reaction and Grignard reaction with the last segment (Grignard reangent segment) to synthesize the final product P1, the above mentioned work is ongoing till now. We have completed 12 steps of the synthesis(The total synthetic route is constitueted by 19 steps), including Wittig reaction, photocyclization reaction(two key steps). And 39 compounds, among which 6 are new ones, have been synthesized with reletive spectra data.
Chapter 2. Studies on the Stilbenes Derivatives as Key Intermediates of P1 With the brief review of the methods for making stilbenes, Wittig reaction has been chosen as the key coupling step finally. And a systematic study has been taken on this step. By the experiments results of Wittig reactions, an optimalized route and proper conditions have been decided, then a series of stilbenes have been made, which are precursor of the photocyclization reaction.
引文
[1]徐战；李德远；农牧产品开发,1999年1期,3-5页.
[2]Ke Li,Xiao-Ming Li,Nai-Yun Ji,James B. Gloer,Bin-Gui Wang,Org. Lett., 2008,10,1429-1432.
[3]Duan, X. J.; Zhang, W. W.; Li, X. M.; Wang, B. G, Food Chem.2006,95,37-43.
[4]梁云；王洪新,Journal of Anhui Agri.Sci.,2008,36,2181-2183.
[5]Takahachi Shimizu,Takaaki Horaguchi and Akio Watanabe, Bull. Chem. Soc. Jpn.1973,46,1772-1776.
[6]Bai, L.; Yamaki M.; Takagi, S., Phytochemistry 1996,42,853-856.
[7]Liu, Q. W.; Tan, C. H.; Zhang, T.; Zhang, S. J.; Han, L. J.; Fan,X.; Zhu, D. Y., J. Asian Nat. Prod. Res.2006,8,379-383.
[8]Li, K.; Li, X. M.; Ji, N. Y.; Wang, B. G, Bioorg. Med. Chem.2007,15,6627-6631.
[9]Li, K.; Li, X. M.; Ji, N. Y.; Wang, B. G, J. Nat. Prod.2008,71,28-30.
[10]Takagi, S.; Yamaki, M.; Inoue, K., Phytochemistry 1983,22,1011-1015.
[11]Bai, L.; Kato, T.; Inoue, K.; Yamaki, M.; Takagi, S. Phytochemistry.1991,30, 2733-2735.
[12]Yamaki, M.; Kato, T.; Bai, L.; Inoue, K.; Takagi, S., Phytochemistry.1993,34, 535-537.
[13]Bai, L.; Yamaki, M.; Takagi, S., Phytochemistry.1996,42,853-856.
[14]Lin, Y L.; Huang, R. L.; Don, M. J.; Kuo, Y. H., J. Nat. Prod.2000,53,1608-1610
[15]Aknin, M.; Samb, A.; Mirailles, J.; Costantino, V.; Fattorusso, E.;Mangoni A., Tetrahedron Lett.1992,33,555-558.
[16]Ma, M.; Zhao, J. L.; Wang, S. J.; Li, S.; Yang, Y C.; Shi, J. G.;Fan, X.; He L., J. Nat. Prod.2006,69,206-210.
[17]Kurata K.; Taniguchii K.; Takashima K.; Hayashi I.; Suzuki M.,Phytochemistry 1997,45,485-487.
[18]Kurihara, H.; Mitani, T.; Kawabata, J.; Takahashi, K. J. Nat. Prod.1999,62,882-884.
[19]Kubo, I.; Ochi, M.; Shibata, K.; Hanke, F. J.; Nakatsu, T.; Tan, K.S.; Taniguchi, M.; Kamikawa, T.; Yamagiwa, Y.; Arizuka, M.; Wood, W.F. J. Nat. Prod.1990,53,50-56.
[20]A.V.Dendy,J.H.P.Tyman,and W.B.Wahlley,J.Chem.Soc.,1963,4040.
[21]Horaguchi, T.; Shimizu, T. Bull. Chem. Soc. Jpn.1974,47,485-487.
[22]O.Fischer,Vongerichten,Ber.,19,1886,792.
[23]Frank B.Mallory,Kelly E.Butler.Tetrahedron,2001,57,3715-3724.
[24]Faouzi Aloui and Riadh El Abed. Synthetic Communications, 2006,36,1557-1567.
[25]J.C. Roberts and J.A. Pincock. Can. J. Chem. Vol.81,2003
[26]Keira Gaukroger,John A Hadfield,Nicholas J Lawrence,Steven Nolan, Alan T McGown.,Org. Biomol. Chem.,2003,1,3033-3037.
[27]Yali Kong,Jolanta Grembecka,Michael C. Edler,Ernest Hamel, Susan L. Mooberry,Michal Sabat,Jayson Rieger,and Milton L. Brown.,Chemistry & Biology,2005,12,1007-1014.
[28]George R. Pettit, Monte R. Rhodes, Delbert L. Herald, Ernest Hamel, Jean M. Schmidt, and Robin K. Pettit.J. Med. Chem.2005,48,4087-4099.
[29]Wenling Li, Hao Li, Ying Li, and Zijie Hou.Angew. Chem. Int. Ed., 2006,45,7609-7611.
[30]Ashraful Alam,Yutaka Takaguchi,Hideyuki Ito,Takashi Yoshidab, Sadao Tsuboi.Tetrahedron,2005,61,1909-1918.
[31]Sylvie Radixa,Roland Barret.Tetrahedron,2007,63,12379-12387.
[32]Junbiao Chang,Xiaohe Guo,Senxiang Cheng,Ruiyun Guo,Rongfeng Chen, Kang Zhao.Bioorg. Med. Chem. Lett.,2004,14,2131-2136.
[33]George R.,Pettit,Sheo Bux Singh.CAN. J. CHEM. VOL.65,1987
[34]Wei-Ge Zhang,Rui Zhao, Jian Ren, Li-Xiang Ren,Jin-Guang Lin, Dai-Lin Liu,Ying-Liang Wu,Xin-Sheng Yao.Arch. Pharm. Chem. Life Sci., 2007,340,244-250.
[35]Vandana Srivastava, Mahendra P. Darokar, Atiya Fatima, J. K. Kumar,Chinmay Chowdhury, Hari Om Saxena, Gaurav R. Dwivedi, Kunal Shrivastava.Bioorganic & Medicinal Chemistry,2007,15,518-525.
[36]Jian Yang, LingLing Weng, and Hu Zheng,Synthetic Communications, 2006,36,2401-2405.
[37]Benjamin A. Horenstein, and Koji Nakanishi.J. Am. Chem. Soc.,1989,111 (16), 6242-6246.
[38]Chai-Lin Kao and Ji-Wang Chern.J. Org. Chem.2002,67,6772-6787.
[39]A. Srikrishna, G. Satyanarayana.Tetrahedron,2006,62,2892-2900.
[40]Paul B. Huleatt, Sze Shiong Choo, Sheena Chua, Christina L. L. Chai.Tetrahedron Letters,2008,49,5309-5311.
[41]Nagwa A. Shoeib,Michael C. Bibby,erald Blunden,Peter A. Linley,David J. Swaine,Richard T. Wheelhouse,Colin W.WrightJ. Nat. Prod.,2004,67,1445-1449.
[42]G. Vallejos.Bioorg. Med. Chem.,2005,13,4450-4457.
[43]AJAM C. Shaikh, Yuyun Wang and Chinpiao Chen.J Label Compd Radiopharm 2007,50,660-665.
[44]Nolan R. Mente, Jeffrey D. Neighbors, and David F. Wiemer.J. Org. Chem.,2008, 73,7963-7970.
[45]V. Percec,W.-D. Cho.J. Am. Chem. Soc.,1998,120,11061-11070.
[46]Hong Bin Zou,Sheng Yi Dong,Chang Xin Zhou.Bioorganic & Medicinal Chemistry,2006,14,2060-2071.
[47]Virgil Percec,Betty C. Won,Mihai Peterca,and Paul A. Heiney.J. Amer. Chem. Soc.,2007,129,11265-11278.
[48]F. B. Mallory, C. S. Wood, and J. T. Gordon, J. Amer. Chem.Soc.,1964,86,3094.
[49]W. M. Moore, D. D. Morgan, and F. R. Stermitz, ibid.,1963,85,828.
[50]K. A. Muszkat and E. Fisher, J. Chem. SOC. B,1967,662.
[51]Jurd, L. J. Am. Chem. Soc.,1959,81,4606-4610.
[52]Cardona, M. L.; Fernandez, M. I.; Garcia, M. B.; Pedro, J. R.Tetrahedron,1986,42, 2725
[53]Davis, F. A.; Fanelli, D. L. J. Org. Chem.,1998,63,1981.
[54]Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc.,1996,118,9202.
[55]J. Chang.Bioorg. Med. Chem. Lett.,2004,14,2131-2136.
[56]Shizuka Saito,Hong Gao,Jun Kawabata.Helvetica Chimica Acta,2006,89,821-831.
[57]Hyun Jung Lee,Jai Woong Seo,Bong Ho Lee,Kyoo-Hyun Chunga,Dae Yoon Chi.,Bioorganic & Medicinal Chemistry Letters,2004,14,463-466.
[58]Said Eddarir,Zouanate Abdelhadib,Christian Rolando, Tetrahedron Letters,2001,42,9127-9130.
[59]F. R. Stermitz, Org. Photochem.,1967,1,247.
[60]W. M. Horspool, J. Chem. Soc. C,1971,400.
[61]Lutz M. Engelhardt, Frank R. Hewgill,Jeffery M. Stewart, and Allan H. White.J. Chem. Soc. PERKIN TRANS.I,1988,1845-1850.
[62]Frank R. Hewgill and Jeffery M. Stewart.,J. Chem. soc. PERKIN TRANS. I,1988,1305-1311.
[63]Gabriel Vallejos,Angelica Fierro,Marcos Caroli Rezende,Silvia Sepulveda-Bozab and Miguel Reyes-Parada.Bioorg. Med. Chem.,2005,13,4450-4457.
[64]H. Stegemeyer, Z. Naturforsch. Teil B,1962,17,153.
[65]Ch. Goedicke and H. Stegemeyer, Ber. Bunsenges. Phys. Chem.,1969,73,782.
[66]F. B. Mallory, C. S. Wood, J. T. Gordon, L. C. Lindquist, and M. L. Savitz,J. Am. Chem. Soc.,1962,84,4361.
[67]W. M. Moore, D. D. Morgan, and F. R. Stermitz, J. Am. Chem. Soc.,1963,85,829.
[68]F. B. Mallory, C. S. Wood, and J. T. Gordon, J. Am. Chem. Soc.,1964,86,3094.
[69]G. S. Hammond, J. Saltiel, A. A. Lamola, N. J. Turro, J. S. Bradshaw, D.O. Cowan, R. C. Counsell, V. Vogt, and C. Dalton, J. Am. Chem. Soc.,1964,86,3197.
[70]A. A. Lamola, G. S. Hammond, and F. B. Mallory, Photochem. Photobiol.,1965,4, 259.
[71]E. V. Blackburn and C. J. Timmons, Quart. Rev., Chem. Soc.,1969,23,482.
[72]M. Scholz, F. Dietz, and M. Muhlstdt, Z. Chem.,1967,7,329.
[73]E. Fischer, Mol. Photochem.,1973,5,227.
[74]J. Saltiel, Mol. Photochem.,1973,5,231.
[75]J. Saltiel, D. W.-L. Chang, and E. D.Megarity, J. Am. Chem. Soc.,1974,96,6521.
[76]F. Momicchioli, M. C. Bruni, I. Baraldi, and G. R. Corradini, J. Chem.Soc., Faraday Trans 2,1974,1325.
[77]K. A. Muszkat and E. Fischer, J. Chem. Soc. B,1967,662.
[78]A. Bromberg, K. A. Muszkat, and E. Fischer, Isr. J. Chem.,1972,10,765.
[79]T. Knittel-Wismonsky, G. Fischer, and E. Fischer, Tetrahedron Lett.,1972,2853.
[80]G. M. Badger, R. J. Drewer, and G. E. Lewis, Aust. J. Chem.,1966,19,643.
[81]K. A. Muszkat and E. Fischer, J. Chem. Soc. B,1967,662.
[82]J. Saltiel, J. Am. Chem. Soc.,1968,90,6394.
[83]A. Bylina and Z. R. Grabowski, Trans. Faraday Soc.,1969,65,458.
[84]T.D.Doyle, N. Filipescu, W. R. Benson, and D. Banes, J. Am. Chem.Soc., 1970,92,6371.
[85]A. Schonberg, Preparative Organic Photochemistry, Springer-Verlag,New York, 1968,127-145.
[86]P. G. Sammes, Quart. Rev., Chem. Soc.,1970,24,37.
[87]G Kaupp,Angew. Chem., Int. Ed. Engl.,1980,19,243.
[88]S. W. Benson, J. Chem. Educ.,1965,42,502.
[89]E. V. Blackburn, C. E. Loader, and C. J. Timmons, J. Chem. Soc. C,1968,1576.
[90]G. Ciamician and P. Silber, Chem. Ber.,1902,35,4128.
[91]R. A. Caldwell, K. Mizuno, P. E. Hansen, L. P. Vo, M. Frentrup, and C.D. Ho, J. Am. Chem. Soc.,1981,103,7263.
[92]R. Koussini, R. Lapouyade,P. Fornier de Violet, J. Am. Chem.Soc.,1978,100,6679.
[93]Chai-Lin Kao and Ji-Wang Chern.J. Org. Chem.,2002,67,6772-6787.
[1]S. A. Adesanya,R. Nia, T. M. Martin, N. Boukamcha, A.Montagnac,M. Pais, J. Nat. Prod.,1999,62,1694.
[2]G. G. Dark, S. A. Hill, V. E. Prise, G M. Tozer, G R. Pettit and D. J. Chaplin, Cancer Res.,1997,57,1829.
[3]Singh, S. B.; Pettit, G R. Synth. Commun.,1987,17,877-892.
[4]Xavier Vitrac,Alexis Desmouliere.Life Sciences,2003,72,2219-2233.
[5]J. A. Hadfield, S.Ducki,N.Hirst and A.T.McGown,Prog. Cell.Cycle Res.,2003,5,309.
[6]A. M. Jordan, J. A. Hadfield, N. J. Lawrence and A. T. McGown,Med. Res. Rev.,1998, 259-296.
[7]M. Cushman, D. Nagarathnam, D. Gopal, H-M. He, C. M. Lin and E. Hamel, J. Med. Chem.,1992,35,2293.
[8]Pinney, K. G.; Bounds, A. D.; Dingeman, K. M.; Mocharla,V. P.; Pettit, G R.; Bai, R.; Hamel, E. Bioorg. Med.Chem. Lett.,1999,9,1081-1086.
[9]Aleksandrzak,K.;McGown,A.T.; Hadfield, J. A. Anti-Cancer Drugs,1998,9,545-550.
[10]H.-F. Luo,L.-P. Zhang, C.-Q. Hu, Tetrahedron,2001,57,48 49.
[11]George R. Pettit,Monte R. Rhodes,Delbert L. Herald,Ernest Hamel,J. Med. Chem., 2005,48,4087-4099
[12]Yanlong, Q.; Guisheng, L.; Huang, Y. J. Organomet. Chem.,1990,381,29-34.
[13]Alonso,D.A.; Fuensanta,M.;Najera,C.;Varea,M.J. Org. Chem.,2005,70,6404-6416.
[14]Mongkol Sukwattanasinitt. Tetrahedron Letters,2001,42,5291-5293.
[15]Inaba, S.; Matsumoto, H.; Rieke, R. D. J. Org. Chem.,1984,49,2093-2098.
[16]Aitken, R. A; Hodgson, P. K. G.; Morrison, J. J.; Oyewale, A. O. J.Chem. Soc, Perkin Trans.1,2002,3,402-415.
[17]De Sa, A. C. P. F.; Pontes, G. M. A.; Dos Anjos, J. A. L.; Santana,S. R.; Bieber, L. W.; Malvestiti, I. J. Braz. Chem. Soc.,2003,14,429-434.
[18]Krief, A.; Laval, A.-M. Chem. ReV.,1999,99,745-777.
[19]Ma, J.; Chan, T.-H. Tetrahedron Lett.,1998,39,2499-2502.
[20]Shey, J.; McGinley, C. M.; Mcauley, K. M.; Dearth, A. S.; Young,B.; van der Donk, W. A. J. Org. Chem.,2002,67,837-846.
[21]Paolo Lupattelli,Maurizio D'Auria,Nadia Di Blasio,nd Francesca Lenti.Eur. J. Org. Chem.,2009,141-145
[22]Chul-HeeCho,Chul-Bae Kim,and Kwangyong Park.J.Comb.Chem.,2010,12,45-50.
[23]G. R. Pettit, S. B. Singh, M. R. Boyd, E. Harnel, R. K. Pettit,J. M. Schmidt, F. Hogan, J. Med. Chem.,1995,38,1666-1672.
[24]Dambacher,Tetrahedron Lett.,2005,46,4473.
[25]Jinhua J. Song,Nathan K. Yee, Zhulin Tan, Jinghua Xu, Suresh R. Kapadia, andChris H. Senanayake.Org. Lett., Vol.6, No.26,2004,4905-4907.
[26]Alexandre Bouillon,Tetrahedron,2002,58,2885-2890.
[27]E. Hedaya and S. Theodoropulos.Tetrahedron,1968,24,2241-2254.
[2]Ke Li,Xiao-Ming Li,Nai-Yun Ji,James B. Gloer,Bin-Gui Wang,Org. Lett., 2008,10,1429-1432.
[3]Duan, X. J.; Zhang, W. W.; Li, X. M.; Wang, B. G, Food Chem.2006,95,37-43.
[4]梁云；王洪新,Journal of Anhui Agri.Sci.,2008,36,2181-2183.
[5]Takahachi Shimizu,Takaaki Horaguchi and Akio Watanabe, Bull. Chem. Soc. Jpn.1973,46,1772-1776.
[6]Bai, L.; Yamaki M.; Takagi, S., Phytochemistry 1996,42,853-856.
[7]Liu, Q. W.; Tan, C. H.; Zhang, T.; Zhang, S. J.; Han, L. J.; Fan,X.; Zhu, D. Y., J. Asian Nat. Prod. Res.2006,8,379-383.
[8]Li, K.; Li, X. M.; Ji, N. Y.; Wang, B. G, Bioorg. Med. Chem.2007,15,6627-6631.
[9]Li, K.; Li, X. M.; Ji, N. Y.; Wang, B. G, J. Nat. Prod.2008,71,28-30.
[10]Takagi, S.; Yamaki, M.; Inoue, K., Phytochemistry 1983,22,1011-1015.
[11]Bai, L.; Kato, T.; Inoue, K.; Yamaki, M.; Takagi, S. Phytochemistry.1991,30, 2733-2735.
[12]Yamaki, M.; Kato, T.; Bai, L.; Inoue, K.; Takagi, S., Phytochemistry.1993,34, 535-537.
[13]Bai, L.; Yamaki, M.; Takagi, S., Phytochemistry.1996,42,853-856.
[14]Lin, Y L.; Huang, R. L.; Don, M. J.; Kuo, Y. H., J. Nat. Prod.2000,53,1608-1610
[15]Aknin, M.; Samb, A.; Mirailles, J.; Costantino, V.; Fattorusso, E.;Mangoni A., Tetrahedron Lett.1992,33,555-558.
[16]Ma, M.; Zhao, J. L.; Wang, S. J.; Li, S.; Yang, Y C.; Shi, J. G.;Fan, X.; He L., J. Nat. Prod.2006,69,206-210.
[17]Kurata K.; Taniguchii K.; Takashima K.; Hayashi I.; Suzuki M.,Phytochemistry 1997,45,485-487.
[18]Kurihara, H.; Mitani, T.; Kawabata, J.; Takahashi, K. J. Nat. Prod.1999,62,882-884.
[19]Kubo, I.; Ochi, M.; Shibata, K.; Hanke, F. J.; Nakatsu, T.; Tan, K.S.; Taniguchi, M.; Kamikawa, T.; Yamagiwa, Y.; Arizuka, M.; Wood, W.F. J. Nat. Prod.1990,53,50-56.
[20]A.V.Dendy,J.H.P.Tyman,and W.B.Wahlley,J.Chem.Soc.,1963,4040.
[21]Horaguchi, T.; Shimizu, T. Bull. Chem. Soc. Jpn.1974,47,485-487.
[22]O.Fischer,Vongerichten,Ber.,19,1886,792.
[23]Frank B.Mallory,Kelly E.Butler.Tetrahedron,2001,57,3715-3724.
[24]Faouzi Aloui and Riadh El Abed. Synthetic Communications, 2006,36,1557-1567.
[25]J.C. Roberts and J.A. Pincock. Can. J. Chem. Vol.81,2003
[26]Keira Gaukroger,John A Hadfield,Nicholas J Lawrence,Steven Nolan, Alan T McGown.,Org. Biomol. Chem.,2003,1,3033-3037.
[27]Yali Kong,Jolanta Grembecka,Michael C. Edler,Ernest Hamel, Susan L. Mooberry,Michal Sabat,Jayson Rieger,and Milton L. Brown.,Chemistry & Biology,2005,12,1007-1014.
[28]George R. Pettit, Monte R. Rhodes, Delbert L. Herald, Ernest Hamel, Jean M. Schmidt, and Robin K. Pettit.J. Med. Chem.2005,48,4087-4099.
[29]Wenling Li, Hao Li, Ying Li, and Zijie Hou.Angew. Chem. Int. Ed., 2006,45,7609-7611.
[30]Ashraful Alam,Yutaka Takaguchi,Hideyuki Ito,Takashi Yoshidab, Sadao Tsuboi.Tetrahedron,2005,61,1909-1918.
[31]Sylvie Radixa,Roland Barret.Tetrahedron,2007,63,12379-12387.
[32]Junbiao Chang,Xiaohe Guo,Senxiang Cheng,Ruiyun Guo,Rongfeng Chen, Kang Zhao.Bioorg. Med. Chem. Lett.,2004,14,2131-2136.
[33]George R.,Pettit,Sheo Bux Singh.CAN. J. CHEM. VOL.65,1987
[34]Wei-Ge Zhang,Rui Zhao, Jian Ren, Li-Xiang Ren,Jin-Guang Lin, Dai-Lin Liu,Ying-Liang Wu,Xin-Sheng Yao.Arch. Pharm. Chem. Life Sci., 2007,340,244-250.
[35]Vandana Srivastava, Mahendra P. Darokar, Atiya Fatima, J. K. Kumar,Chinmay Chowdhury, Hari Om Saxena, Gaurav R. Dwivedi, Kunal Shrivastava.Bioorganic & Medicinal Chemistry,2007,15,518-525.
[36]Jian Yang, LingLing Weng, and Hu Zheng,Synthetic Communications, 2006,36,2401-2405.
[37]Benjamin A. Horenstein, and Koji Nakanishi.J. Am. Chem. Soc.,1989,111 (16), 6242-6246.
[38]Chai-Lin Kao and Ji-Wang Chern.J. Org. Chem.2002,67,6772-6787.
[39]A. Srikrishna, G. Satyanarayana.Tetrahedron,2006,62,2892-2900.
[40]Paul B. Huleatt, Sze Shiong Choo, Sheena Chua, Christina L. L. Chai.Tetrahedron Letters,2008,49,5309-5311.
[41]Nagwa A. Shoeib,Michael C. Bibby,erald Blunden,Peter A. Linley,David J. Swaine,Richard T. Wheelhouse,Colin W.WrightJ. Nat. Prod.,2004,67,1445-1449.
[42]G. Vallejos.Bioorg. Med. Chem.,2005,13,4450-4457.
[43]AJAM C. Shaikh, Yuyun Wang and Chinpiao Chen.J Label Compd Radiopharm 2007,50,660-665.
[44]Nolan R. Mente, Jeffrey D. Neighbors, and David F. Wiemer.J. Org. Chem.,2008, 73,7963-7970.
[45]V. Percec,W.-D. Cho.J. Am. Chem. Soc.,1998,120,11061-11070.
[46]Hong Bin Zou,Sheng Yi Dong,Chang Xin Zhou.Bioorganic & Medicinal Chemistry,2006,14,2060-2071.
[47]Virgil Percec,Betty C. Won,Mihai Peterca,and Paul A. Heiney.J. Amer. Chem. Soc.,2007,129,11265-11278.
[48]F. B. Mallory, C. S. Wood, and J. T. Gordon, J. Amer. Chem.Soc.,1964,86,3094.
[49]W. M. Moore, D. D. Morgan, and F. R. Stermitz, ibid.,1963,85,828.
[50]K. A. Muszkat and E. Fisher, J. Chem. SOC. B,1967,662.
[51]Jurd, L. J. Am. Chem. Soc.,1959,81,4606-4610.
[52]Cardona, M. L.; Fernandez, M. I.; Garcia, M. B.; Pedro, J. R.Tetrahedron,1986,42, 2725
[53]Davis, F. A.; Fanelli, D. L. J. Org. Chem.,1998,63,1981.
[54]Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc.,1996,118,9202.
[55]J. Chang.Bioorg. Med. Chem. Lett.,2004,14,2131-2136.
[56]Shizuka Saito,Hong Gao,Jun Kawabata.Helvetica Chimica Acta,2006,89,821-831.
[57]Hyun Jung Lee,Jai Woong Seo,Bong Ho Lee,Kyoo-Hyun Chunga,Dae Yoon Chi.,Bioorganic & Medicinal Chemistry Letters,2004,14,463-466.
[58]Said Eddarir,Zouanate Abdelhadib,Christian Rolando, Tetrahedron Letters,2001,42,9127-9130.
[59]F. R. Stermitz, Org. Photochem.,1967,1,247.
[60]W. M. Horspool, J. Chem. Soc. C,1971,400.
[61]Lutz M. Engelhardt, Frank R. Hewgill,Jeffery M. Stewart, and Allan H. White.J. Chem. Soc. PERKIN TRANS.I,1988,1845-1850.
[62]Frank R. Hewgill and Jeffery M. Stewart.,J. Chem. soc. PERKIN TRANS. I,1988,1305-1311.
[63]Gabriel Vallejos,Angelica Fierro,Marcos Caroli Rezende,Silvia Sepulveda-Bozab and Miguel Reyes-Parada.Bioorg. Med. Chem.,2005,13,4450-4457.
[64]H. Stegemeyer, Z. Naturforsch. Teil B,1962,17,153.
[65]Ch. Goedicke and H. Stegemeyer, Ber. Bunsenges. Phys. Chem.,1969,73,782.
[66]F. B. Mallory, C. S. Wood, J. T. Gordon, L. C. Lindquist, and M. L. Savitz,J. Am. Chem. Soc.,1962,84,4361.
[67]W. M. Moore, D. D. Morgan, and F. R. Stermitz, J. Am. Chem. Soc.,1963,85,829.
[68]F. B. Mallory, C. S. Wood, and J. T. Gordon, J. Am. Chem. Soc.,1964,86,3094.
[69]G. S. Hammond, J. Saltiel, A. A. Lamola, N. J. Turro, J. S. Bradshaw, D.O. Cowan, R. C. Counsell, V. Vogt, and C. Dalton, J. Am. Chem. Soc.,1964,86,3197.
[70]A. A. Lamola, G. S. Hammond, and F. B. Mallory, Photochem. Photobiol.,1965,4, 259.
[71]E. V. Blackburn and C. J. Timmons, Quart. Rev., Chem. Soc.,1969,23,482.
[72]M. Scholz, F. Dietz, and M. Muhlstdt, Z. Chem.,1967,7,329.
[73]E. Fischer, Mol. Photochem.,1973,5,227.
[74]J. Saltiel, Mol. Photochem.,1973,5,231.
[75]J. Saltiel, D. W.-L. Chang, and E. D.Megarity, J. Am. Chem. Soc.,1974,96,6521.
[76]F. Momicchioli, M. C. Bruni, I. Baraldi, and G. R. Corradini, J. Chem.Soc., Faraday Trans 2,1974,1325.
[77]K. A. Muszkat and E. Fischer, J. Chem. Soc. B,1967,662.
[78]A. Bromberg, K. A. Muszkat, and E. Fischer, Isr. J. Chem.,1972,10,765.
[79]T. Knittel-Wismonsky, G. Fischer, and E. Fischer, Tetrahedron Lett.,1972,2853.
[80]G. M. Badger, R. J. Drewer, and G. E. Lewis, Aust. J. Chem.,1966,19,643.
[81]K. A. Muszkat and E. Fischer, J. Chem. Soc. B,1967,662.
[82]J. Saltiel, J. Am. Chem. Soc.,1968,90,6394.
[83]A. Bylina and Z. R. Grabowski, Trans. Faraday Soc.,1969,65,458.
[84]T.D.Doyle, N. Filipescu, W. R. Benson, and D. Banes, J. Am. Chem.Soc., 1970,92,6371.
[85]A. Schonberg, Preparative Organic Photochemistry, Springer-Verlag,New York, 1968,127-145.
[86]P. G. Sammes, Quart. Rev., Chem. Soc.,1970,24,37.
[87]G Kaupp,Angew. Chem., Int. Ed. Engl.,1980,19,243.
[88]S. W. Benson, J. Chem. Educ.,1965,42,502.
[89]E. V. Blackburn, C. E. Loader, and C. J. Timmons, J. Chem. Soc. C,1968,1576.
[90]G. Ciamician and P. Silber, Chem. Ber.,1902,35,4128.
[91]R. A. Caldwell, K. Mizuno, P. E. Hansen, L. P. Vo, M. Frentrup, and C.D. Ho, J. Am. Chem. Soc.,1981,103,7263.
[92]R. Koussini, R. Lapouyade,P. Fornier de Violet, J. Am. Chem.Soc.,1978,100,6679.
[93]Chai-Lin Kao and Ji-Wang Chern.J. Org. Chem.,2002,67,6772-6787.
[1]S. A. Adesanya,R. Nia, T. M. Martin, N. Boukamcha, A.Montagnac,M. Pais, J. Nat. Prod.,1999,62,1694.
[2]G. G. Dark, S. A. Hill, V. E. Prise, G M. Tozer, G R. Pettit and D. J. Chaplin, Cancer Res.,1997,57,1829.
[3]Singh, S. B.; Pettit, G R. Synth. Commun.,1987,17,877-892.
[4]Xavier Vitrac,Alexis Desmouliere.Life Sciences,2003,72,2219-2233.
[5]J. A. Hadfield, S.Ducki,N.Hirst and A.T.McGown,Prog. Cell.Cycle Res.,2003,5,309.
[6]A. M. Jordan, J. A. Hadfield, N. J. Lawrence and A. T. McGown,Med. Res. Rev.,1998, 259-296.
[7]M. Cushman, D. Nagarathnam, D. Gopal, H-M. He, C. M. Lin and E. Hamel, J. Med. Chem.,1992,35,2293.
[8]Pinney, K. G.; Bounds, A. D.; Dingeman, K. M.; Mocharla,V. P.; Pettit, G R.; Bai, R.; Hamel, E. Bioorg. Med.Chem. Lett.,1999,9,1081-1086.
[9]Aleksandrzak,K.;McGown,A.T.; Hadfield, J. A. Anti-Cancer Drugs,1998,9,545-550.
[10]H.-F. Luo,L.-P. Zhang, C.-Q. Hu, Tetrahedron,2001,57,48 49.
[11]George R. Pettit,Monte R. Rhodes,Delbert L. Herald,Ernest Hamel,J. Med. Chem., 2005,48,4087-4099
[12]Yanlong, Q.; Guisheng, L.; Huang, Y. J. Organomet. Chem.,1990,381,29-34.
[13]Alonso,D.A.; Fuensanta,M.;Najera,C.;Varea,M.J. Org. Chem.,2005,70,6404-6416.
[14]Mongkol Sukwattanasinitt. Tetrahedron Letters,2001,42,5291-5293.
[15]Inaba, S.; Matsumoto, H.; Rieke, R. D. J. Org. Chem.,1984,49,2093-2098.
[16]Aitken, R. A; Hodgson, P. K. G.; Morrison, J. J.; Oyewale, A. O. J.Chem. Soc, Perkin Trans.1,2002,3,402-415.
[17]De Sa, A. C. P. F.; Pontes, G. M. A.; Dos Anjos, J. A. L.; Santana,S. R.; Bieber, L. W.; Malvestiti, I. J. Braz. Chem. Soc.,2003,14,429-434.
[18]Krief, A.; Laval, A.-M. Chem. ReV.,1999,99,745-777.
[19]Ma, J.; Chan, T.-H. Tetrahedron Lett.,1998,39,2499-2502.
[20]Shey, J.; McGinley, C. M.; Mcauley, K. M.; Dearth, A. S.; Young,B.; van der Donk, W. A. J. Org. Chem.,2002,67,837-846.
[21]Paolo Lupattelli,Maurizio D'Auria,Nadia Di Blasio,nd Francesca Lenti.Eur. J. Org. Chem.,2009,141-145
[22]Chul-HeeCho,Chul-Bae Kim,and Kwangyong Park.J.Comb.Chem.,2010,12,45-50.
[23]G. R. Pettit, S. B. Singh, M. R. Boyd, E. Harnel, R. K. Pettit,J. M. Schmidt, F. Hogan, J. Med. Chem.,1995,38,1666-1672.
[24]Dambacher,Tetrahedron Lett.,2005,46,4473.
[25]Jinhua J. Song,Nathan K. Yee, Zhulin Tan, Jinghua Xu, Suresh R. Kapadia, andChris H. Senanayake.Org. Lett., Vol.6, No.26,2004,4905-4907.
[26]Alexandre Bouillon,Tetrahedron,2002,58,2885-2890.
[27]E. Hedaya and S. Theodoropulos.Tetrahedron,1968,24,2241-2254.