Chemoenzymatic total synthesis of potent HIV RNase H inhibitor (−)-1,3,4,5-tetragalloylapiitol
作者： Ramesh U. Batwal , Ramesh M. Patel , Narshinha P. Argade
DOI: 10.1016/J.TETASY.2010.11.032
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摘要: Abstract Starting from racemic dimethyl 2-acetoxy-3-methylenesuccinate, the chemoenzymatic facile total synthesis of ( − )-1,3,4,5-tetragalloylapiitol has been demonstrated via an efficient lipase catalyzed resolution followed by a DIBAL reduction–double gallyolation, osmium tetroxide dihydroxylation–double and reductive global O -benzyl deprotection pathway.
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sci-hub.se 参考文章(26)
Umesh A. Kshirsagar, Vedavati G. Puranik, Narshinha P. Argade, Total Synthesis of Proposed Auranthine Journal of Organic Chemistry. ,vol. 75, pp. 2702- 2705 ,(2010) , 10.1021/JO100400Z
Edward Arnold, Alfredo Jacobo-Molina, Raymond G. Nanni, Roger L. Williams, Xiaode Lu, Jianping Ding, Arthur D. Clark Jr, Anqiang Zhang, Andrea L. Ferris, Patrick Clark, Amnon Hizi, Stephen H. Hughes, Structure of HIV-1 reverse transcriptase/DNA complex at 7 Å resolution showing active site locations Nature. ,vol. 357, pp. 85- 89 ,(1992) , 10.1038/357085A0
Mandeep Singh, Narshinha P. Argade, Chemoselective coupling reactions of 5,7-dimethoxyphthalide with the remotely functionalized alkyl iodides: facile racemic synthesis of Helicobacter pylori antibiotics. Journal of Organic Chemistry. ,vol. 75, pp. 3121- 3124 ,(2010) , 10.1021/JO100168F
Tomozumi Imamichi, Action of Anti-HIV Drugs and Resistance: Reverse Transcriptase Inhibitors and Protease Inhibitors Current Pharmaceutical Design. ,vol. 10, pp. 4039- 4053 ,(2004) , 10.2174/1381612043382440
Xianbin Su, David S. Surry, Richard J. Spandl, David R. Spring, Total Synthesis of Sanguiin H-5 Organic Letters. ,vol. 10, pp. 2593- 2596 ,(2008) , 10.1021/OL8009545
Srinivasan Easwar, Narshinha P. Argade, Amano PS-catalysed enantioselective acylation of (±)-α-methyl-1,3-benzodioxole-5-ethanol: an efficient resolution of chiral intermediates of the remarkable antiepileptic drug candidate, (−)-talampanel Tetrahedron: Asymmetry. ,vol. 14, pp. 333- 337 ,(2003) , 10.1016/S0957-4166(02)00836-4
George Kraus, Aaron Kempema, A Direct Synthesis of Racemic1,3,4,5-Tetragalloylapiitol Synthesis. ,vol. 2010, pp. 389- 391 ,(2010) , 10.1055/S-0029-1217123
L. Kohlstaedt, J Wang, J. Friedman, P. Rice, T. Steitz, Crystal structure at 3.5 A resolution of HIV-1 reverse transcriptase complexed with an inhibitor. Science. ,vol. 256, pp. 1783- 1790 ,(1992) , 10.1126/SCIENCE.1377403
Jonathan D. Mortison, David H. Sherman, Frontiers and opportunities in chemoenzymatic synthesis. Journal of Organic Chemistry. ,vol. 75, pp. 7041- 7051 ,(2010) , 10.1021/JO101124N
Yvan Guindon, Mohammed Bencheqroun, Abderrahim Bouzide, Synthesis of Postulated Molecular Probes: Stereoselective Free-Radical-MediatedC-Glycosylation in Tandem with Hydrogen Transfer Journal of the American Chemical Society. ,vol. 127, pp. 554- 558 ,(2005) , 10.1021/JA046389Y