Enantioselective total synthesis of the potent Anti-HIV nucleoside EFdA

Organic Letters

Volumn 13, Issue 19, 2011, Pages 5264-5266

  Kageyama, Masayuki ^a   Nagasawa, Tomohiro ^a   Yoshida, Mayumi ^a   Ohrui, Hiroshi ^b   Kuwahara, Shigefumi ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b YOKOHAMA COLLEGE OF PHARMACY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4' ETHYNYL 2 FLUORO 2' DEOXYADENOSINE; 4'-ETHYNYL-2-FLUORO-2'-DEOXYADENOSINE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; DEOXYADENOSINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; STEREOISOMERISM; SYNTHESIS;

ANTI-HIV AGENTS; DEOXYADENOSINES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 80054745392     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202116k     Document Type: Article

References (23)

1. Kohgo, S.; Ohrui, H.; Kodama, E.; Matsuoka,M.; Mitsuya, H. 40-C-Substituted-2-halo-adenosine derivative. Can. Pat. CA 2502109, 2005.
2. Kohgo, S.; Yamada, K.; Kitano, K.; Iwai, Y.; Sakata, S.; Ashida, N.; Hayakawa, H.; Nameki, D.; Kodama, E.; Matsuoka, M.; Mitsuya, H.; Ohrui, H. Nucleosides Nucleotides Nucleic Acids 2004, 23, 671-690.
3. Ohrui, H. Chem. Rec. 2006, 6, 133-143.
4. Ohrui, H.; Hayakawa, H.; Kohgo, S.; Matsuoka, M.; Kodama, E.; Mitsuya, H. J. Synth. Org. Chem. Jpn. 2006, 64, 716-723.
5. Ohrui, H.; Kohgo, S.; Hayakawa, H.; Kodama, E.; Matsuoka, M.; Nakata, T.; Mitsuya, H. Nucleosides Nucleotides Nucleic Acids 2007, 26, 1543-1546.
6. Ohrui, H. Proc. Jpn. Acad., Ser. B 2011, 87, 53-65.
7. Nikolenko, G. N.; Kotelkin, A. T.; Oreshkova, S. F.; Ilyichev, A. A. Mol. Biol. 2011, 45, 93-109.
8. Sharma, B. Neurobehav. HIV Med. 2011, 3, 27-40.
9. Michailidis, E.; Marchand, B.; Kodama, E. N.; Singh, K.; Matsuoka, M.; Kirby, K. A.; Ryan, E. M.; Sawani, A. M.; Nagy, E.; Ashida, N.; Mitsuya, H.; Parniak, M. A.; Sarafianos, S. G. J. Biol. Chem. 2009, 284, 35681-35691.
10. Kawamoto, A.; Kodama, E.; Sarafianos, S. G.; Sakagami, Y.; Kohgo, S.; Kitano, K.; Ashida, N.; Iwai, Y.; Hayakawa, H.; Nakata, H.; Mitsuya, H.; Arnold, E.; Matsuoka, M. Int. J. Biochem. Cell Biol. 2008, 40, 2410-2420.
11. Nakata, H.; Amano, M.; Koh, Y.; Kodama, E.; Yang, G.; Bailey, C. M.; Kohgo, S.; Hayakawa, H.; Matsuoka, M.; Anderson, K. S.; Cheng, Y.-C.; Mitsuya, H. Antimicrob. Agents Chemother. 2007, 51, 2701-2708.
12. Hattori, S.; Ide, K.; Nakata, H.; Harada, H.; Suzu, S.; Ashida, N.; Kohgo, S.; Hayakawa, H.; Mitsuya, H.; Okada, S. Antimicrob. Agents Chemother. 2009, 53, 3887-3893.
13. For examples of diastereoselective addition of acetylide anions to MOM-protected R-hydroxy ketones, see: Maddaford,A.;Wainwright, P.; Glen, R.; Fisher, R.; Dragovich, P. S.; Gonzalez, J.; Kung, P.-P.; Middleton, D. S.; Pryde, D. C.; Stephenson, P. S.; Sutton, S. C. Synthesis 2007, 1378-1384.
14. Druais, V.; Hall,M. J.; Corsi, C.; Wendeborn, S. V.; Meyer, C.; Cossy, J. Tetrahedron 2010, 66, 6358-6375.
15. Reddy, B. V. S.; Reddy, B. P.; Pandurangam, T.; Yadav, J. S. Tetrahedron Lett. 2011, 52, 2306-2308.
16. Nagaiah, K.; Sreenu, D.; Purnima, K. V.; Rao, R. S.; Yadav, J. S. Synthesis 2009, 1386-1392.
17. Einhorn, C.; Luche, J.-L. J. Organomet. Chem. 1987, 322, 177-183.
18. 2/n-PrSH to deprotect MOM ethers, see: Sohn, J.-H.; Waizumi, N.; Zhong, H. M.; Rawal, V. H. J. Am. Chem. Soc. 2005, 127, 7290-7291.
19. Han, J. H.; Kwon, Y. E.; Sohn, J.-H.; Ryu, D. H. Tetrahedron 2010, 66, 1673-1677.
20. For diagnostic NOE correlations in the anomers of 14 and 15, see the Supporting Information. Wright, G E.; Dudycz, L. W. J. Med. Chem. 1984, 27, 175-181.
21. 7-glycosyl isomer of 16 was detected in this reaction.
22. Zhang, W.; Robins, M. J. Tetrahedron Lett. 1992, 33, 1177-1180.
23. Kaburagi, Y.; Kishi, Y. Org. Lett. 2007, 9, 723-826.