Kageyama Masayuki, Miyagi Takuho, Yoshida Mayumi, Nagasawa Tomohiro, Ohrui Hiroshi, Kuwahara Shigefumi
Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Sendai, Japan.
Biosci Biotechnol Biochem. 2012;76(6):1219-25. doi: 10.1271/bbb.120134. Epub 2012 Jun 7.
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%.
EFdA（4'-乙炔基-2-氟-2'-脱氧腺苷）是一种具有极强抗HIV活性的核苷逆转录酶抑制剂，它由（R）-甘油醛丙酮化物经12步反应简洁合成，总收率为18%，其中涉及α-烷氧基酮中间体的高度非对映选择性乙炔化反应。本合成方法在总收率和步骤数方面均优于之前的方法，之前的方法从昂贵的起始原料开始需要18步反应，总收率仅为2.5%。
