Concise synthesis of (±)-Lingzhiol via epoxy-arene cyclization
作者： Dong Chen , Hao-Miao Liu , Ming-Ming Li , Yong-Min Yan , Wen-Dan Xu
DOI: 10.1039/C5CC05680B
关键词:
摘要: Concise synthesis of (±)-Lingzhiol has been achieved. The key reaction involves one-step construction a 5/5/6/6 tetra-ring backbone Lingzhiol via epoxy-arene cyclization.
rsc.org
sci-hub.se 参考文章(17)
Rong Long, Jun Huang, Wenbin Shao, Song Liu, Yu Lan, Jianxian Gong, Zhen Yang, Asymmetric total synthesis of (−)-lingzhiol via a Rh-catalysed [3+2] cycloaddition Nature Communications. ,vol. 5, pp. 5707- ,(2014) , 10.1038/NCOMMS6707
K. B. Sharpless, R. F. Lauer, Selenium dioxide oxidation of olefins. Evidence for the intermediacy of allylseleninic acids Journal of the American Chemical Society. ,vol. 94, pp. 7154- 7155 ,(1972) , 10.1021/JA00775A050
K. B. Sharpless, R. C. Michaelson, High stereo- and regioselectivities in the transition metal catalyzed epoxidations of olefinic alcohols by tert-butyl hydroperoxide Journal of the American Chemical Society. ,vol. 95, pp. 6136- 6137 ,(1973) , 10.1021/JA00799A061
Yong-Ming Yan, Jun Ai, Li−Li Zhou, Arthur C.K. Chung, Rong Li, Jing Nie, Ping Fang, Xin-Long Wang, Jie Luo, Qun Hu, Fan-Fan Hou, Yong-Xian Cheng, Lingzhiols, unprecedented rotary door-shaped meroterpenoids as potent and selective inhibitors of p-Smad3 from Ganoderma lucidum. Organic Letters. ,vol. 15, pp. 5488- 5491 ,(2013) , 10.1021/OL4026364
Stephen K. Taylor, Mark E. Davisson, B. Rolf Hissom, Sandra L. Brown, Holle A. Pristach, Scott B. Schramm, Suzanne M. Harvey, Friedel-Crafts cyclialkylations of some epoxides. 2. Stereospecificity, substituent, product, and kinetic studies Journal of Organic Chemistry. ,vol. 52, pp. 425- 429 ,(1987) , 10.1021/JO00379A021
Stephen K. Taylor, Curtis L. Blankespoor, Suzanne M. Harvey, Lynell J. Richardson, Friedel-Crafts cyclialkylations of some epoxides. 3. Cyclizations of tertiary and meta-substituted arylalkyl epoxides Journal of Organic Chemistry. ,vol. 53, pp. 3309- 3312 ,(1988) , 10.1021/JO00249A032
Andrew Hinman, J. Du Bois, A stereoselective synthesis of (-)-tetrodotoxin. Journal of the American Chemical Society. ,vol. 125, pp. 11510- 11511 ,(2003) , 10.1021/JA0368305
Stephen K. Taylor, Milica Ivanovic, Lloyd J. Simons, Matthew M. Davis, An efficient asymmetric synthesis of key intermediates in the synthesis of aphanorphine and eptazocine Tetrahedron-asymmetry. ,vol. 14, pp. 743- 747 ,(2003) , 10.1016/S0957-4166(03)00117-4
Sheng-Yuan Wang, Ming-Ling Hsu, Hui-Chi Hsu, Shiuh-Sheng Lee, Ming-Shi Shiao, Chi-Kuan Ho, The anti-tumor effect of Ganoderma lucidum is mediated by cytokines released from activated macrophages and T lymphocytes International Journal of Cancer. ,vol. 70, pp. 699- 705 ,(1997) , 10.1002/(SICI)1097-0215(19970317)70:6<699::AID-IJC12>3.0.CO;2-5
Jer-Min Lin, Chun-Ching Lin, Ming-Feng Chen, Takashi Ujiie, Atsushi Takada, Radical scavenger and antihepatotoxic activity of Ganoderma formosanum, Ganoderma lucidum and Ganoderma neo-japonicum. Journal of Ethnopharmacology. ,vol. 47, pp. 33- 41 ,(1995) , 10.1016/0378-8741(95)01251-8