1400814-13-2Relevant academic research and scientific papers
Concise synthesis of the anti-HIV nucleoside EFdA
Kageyama, Masayuki,Miyagi, Takuho,Yoshida, Mayumi,Nagasawa, Tomohiro,Ohrui, Hiroshi,Kuwahara, Shigefumi
scheme or table, p. 1219 - 1225 (2012/10/18)
EFdA (4'-ethynyl-2-fluoro-2'-deoxyadenosine), a nucleoside reverse transcriptase inhibitor with extremely potent anti-HIV activity, was concisely synthesized from (R)-glyceraldehyde acetonide in an 18% overall yield by a 12-step sequence involving highly diastereoselective ethynylation of an α-alkoxy ketone intermediate. The present synthesis is superior, both in overall yield and in the number of steps, to the previous one which required 18 steps from an expensive starting material and resulted in a modest overall yield of 2.5%.
