Stereoselective synthesis of alkynyl C-2-deoxy-beta-d-ribofuranosides via intramolecular nicholas reaction: A versatile building block for nonnatural C-nucleosides
Takase, M; Morikawa, T; Abe, H; Inouye, M
| HERO ID | 5416744 |
|---|---|
| In Press | No |
| Year | 2003 |
| Title | Stereoselective synthesis of alkynyl C-2-deoxy-beta-d-ribofuranosides via intramolecular nicholas reaction: A versatile building block for nonnatural C-nucleosides |
| Authors | Takase, M; Morikawa, T; Abe, H; Inouye, M |
| Journal | Organic Letters |
| Volume | 5 |
| Issue | 5 |
| Page Numbers | 625-628 |
| Abstract | The reaction of 3,5-di-O-benzyl-2-deoxy-d-ribofuranose with various alkynyllithium reagents afforded diastereomeric mixtures of the corresponding ring-opened alkynyldiols. The resulting diastereomeric mixtures were successively treated with Co(2)(CO)(8), a catalytic amount of TfOH, Et(3)N, and iodine in one pot to give alkynyl C-3,5-di-O-benzyl-2-deoxy-beta-d-ribofuranosides with high beta-selectivities. The cobalt-mediated cyclization (intramolecular Nicholas reaction) is reversible; thus, thermodynamically more stable beta-anomers were obtained preferentially. The alkynyl C-deoxyribofuranosides were converted to a variety of C-deoxyribofuranoside derivatives. |
| Doi | 10.1021/ol027210w |
| Pmid | 12605475 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |