Diastereoselective synthesis of L-(+)-homolamivudine

Tetrahedron Letters

Volumn 40, Issue 51, 1999, Pages 8989-8992

  Khan, Noshena ^a   Bastola, Shyamal R ^a   Witter, Kevin G ^a   Scheiner, Peter ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LAMIVUDINE;

ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0033579604     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01935-8     Document Type: Article

References (20)

1. a. Staszewski, S.; Loveday, C.; Picazo, J.; et al. J. Am.med. Assoc. 1996, 276, 111-117.
2. b. Hammer, S.M.; Squires, K.E.; Hughes, M.D.; et al. New Engl. J. Med. 1997, 337, 725-733.
3. a. Coates, J.A.V.; Cammack, N.; Jenkenson, H.J.; et al. Antimicrob. Agents Chemother. 1992, 36, 202-205.
4. b. Jeong, L.S.; Schinazi, R.F.; Beach, J.W.; et al. J. Med. Chem. 1993, 36, 2627-2638.
5. Parker, W.B.; Cheng, Y-C. J. Natl. Inst. Health Res. 1994, 6, 57-61.
6. a. Schinazi, R.F.; McMillan, A.; Cannon, D. Antimicrob. Agents Chemother. 1992, 36, 2423-2431.
7. b. Furman, P.A.; Davis, M.; Liotta, D.C.; et al. Antimicrob. Agents Chemother. 1992, 36, 2686-2692.
8. Mansour, T.S.; Jin, H.; Wang, W.; et al. J. Med Chem. 1995, 38, 1-4.
9. For a review see Wang, P.; Hong, J.H.; Cooperwood, J.S.; Chu, C.K. Antiviral Res. 1998, 40, 19-44.
10. Lin, J-S.; Kira, T.; Gullen, E.; et al. J. Med. Chem. 1999, 42, 2212-2217.
11. Choi, W.B.; Wilson, L.J.; Yeola, S.; Liotta, D.C. J. Am. Chem. Soc. 1991, 113, 9377-9379.
12. a. Smith, S.; Sjoberg, B. Ber. 1936, 69, 678-680.
13. b. C.A. 1955, 69, P10361.
14. Anisuzzaman, A.K.M.; Owen, L.N. J. Chem. Soc. (C) 1967, 1021-1026.
15. Zacherie, B.; Gagnon, L.; Attardo, G.; et al. J. Med. Chem. 1997, 40, 2883-2894 reported formation of racemic cis 5 by the same cyclization.
16. Cadet, G.; Chan, C-S.; Daniel, R.Y.; et al. J. Org. Chem.., 1998, 63, 4574-4580.
17. Lin, J-S.; Luo, M-Z.; Liu, M-C.; et al. J. Med. Chem., 1991, 34, 2607-2615.
18. Jeong, L.S.; Schinazi, R.F.; Beach, J.W.; et al. J. Med. Chem. 1993, 36, 181-195.
19. 2 group. Nevertheless, both are L-family nucleosides.
20. 20 = +76.2°.