Radical cyclization studies directed toward the synthesis of BMS-200475 'entecavir': The carbocyclic core

Tetrahedron

Volumn 59, Issue 45, 2003, Pages 9013-9018

  Ziegler, Frederick E ^a   Sarpong, Martha A ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

Hepatitis B virus; Radical cyclization; Thiocarbonate

Indexed keywords

ACETYLENE; ALLYL ALCOHOL; CARBON; DEXTRO DIACETONE GLUCOSE; ENTECAVIR; EPOXIDE; ESTER; GLUCOSE DERIVATIVE; GUANINE; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; MITSUNOBU REACTION; PRIORITY JOURNAL; REDUCTION;

HEPATITIS B VIRUS;

EID: 0142217502     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.02.001     Document Type: Article

References (19)

1. Innaimo S.F., Seifer M., Bisacchi G.S., Strandring D.N., Zahler R., Colonno R. J. Antimicrob. Agents Chemother. 41:1997;1444.
2. Bisacchi G.S., Chao S.T., Bachard C., Daris J.P., Innaimo S., Jacobs G.A., Kocy O., Lapointe P., Martel A., Merchant Z., Slusarchyk W.A., Sundeen J.E., Young M.G., Colonno R., Zahler R. Bioorg. Med. Chem. Lett. 7:1997;127.
3. Rokach J., Khanapure S.P., Hwang S.W., Adiyaman M., Schio L., Fitzgerald G.A. Synthesis. 1998;569.
4. Ziegler F.E., Metcalf C.A., Nangia A., Schulte G. J. Am. Chem. Soc. 115:1993;2581.
5. Clive D.L.J., Magnuson S.R. Tetrahedron Lett. 36:1995;15.
6. Roy B.L., Deslongchamps P. Can. J. Chem. 63:1985;651.
7. Lopez R.M., Hays D.S., Fu G.C. J. Am. Chem. Soc. 119:1997;6949.
8. Eastwood F.W., Harrington K.J., Josan J.S., Pura J.L. Tetrahedron Lett. 1970;5223.
9. Ohira S. Synth. Commun. 19:1989;561.
10. Rajanbabu T.V., Nugent W.A. J. Am. Chem. Soc. 116:1994;986.
11. The low yield (37%) may have been the result of the volatility of the product.
12. For related Ti(III)-initiated cyclizations of epoxy acetylenes, see Gansauer A., Pierobon M. Synlett. 2000;1357.
13. Roy S.C., Rana K.K., Guin C. J. Org. Chem. 67:2002;3242.
14. Mukai C., Uchiyama M., Sakamoto S., Hanaoka M. Tetrahedron Lett. 36:1995;5761.
15. Diaz M., Ferrero M., Fernandez S., Gotor V. Tetrahedron Lett. 41:2000;775.
16. Nakazawa M., Sakamoto Y., Takahashi T., Tomooka K., Ishikawa K., Nakai T. Tetrahedron Lett. 34:1993;5923.
17. Rigby J.H., Warshakoon N.C., Payen A.J. J. Am. Chem. Soc. 121:1999;8237.
18. Rigby J.H., Payen A., Warshakoon N. Tetrahedron Lett. 42:2001;2047.
19. Jeong L.S., Yoo S. J. Bioorg. Med. Chem. Lett. 8:1998;847.