Simple entry to 3'-substituted analogues of anti-HIV agent stavudine based on an anionic O --> C stannyl migration.
Reaction of 5'-O-protected derivatives of the anti-HIV agent stavudine (d4T) with LTMP was investigated with the aim to lithiate the vinylic hydrogens (H-3' and H-2'). When the lithiation of the 5'-O-tert-butyldiphenylsilyl derivative 5 was carried out in the presence of HMPA, an anionic silyl migration took place to give the 3'-C-silylated product 4a. The stannyl version of this reaction was found to be also possible, which has disclosed a highly simple entry to the d4T analogues variously substituted at the 3'-position by manipulating the 3'-C-stannyl d4T as a common intermediate.
Kumamoto
Hiroki
H
School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan. hirotnk@pharm.showa-u.ac.jp
Tanaka
Hiromichi
H
D000838:Anions; D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D008094:Lithium / Q000737:chemistry; D018119:Stavudine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D014753:Vinyl Compounds / Q000737:chemistry
D000838:Anions; D019380:Anti-HIV Agents; D014753:Vinyl Compounds; D008094:Lithium; D018119:Stavudine