From the Ene Reaction of Nitrosocarbonyl Intermediates with 3-Methylbut-2-en-1-ol, a New Class of Purine N,O-Nucleoside Analogues
Quadrelli, P; Mella, M; Carosso, S; Bovio, B
| HERO ID | 2906320 |
|---|---|
| In Press | No |
| Year | 2013 |
| Title | From the Ene Reaction of Nitrosocarbonyl Intermediates with 3-Methylbut-2-en-1-ol, a New Class of Purine N,O-Nucleoside Analogues |
| Authors | Quadrelli, P; Mella, M; Carosso, S; Bovio, B |
| Journal | Synthesis |
| Volume | 45 |
| Issue | 10 |
| Page Numbers | 1414-1420 |
| Abstract | Sterically encumbered nitrosocarbonyl derivatives of mesitylene or anthracene undergo ene reactions with 3-methylbut-2-en-1-ol to give the corresponding the 5-hydroxyisoxazolidine adducts in fair yields. According to the proposed mechanism, these heterocycles are derived from the anti-Markovnikov orientation of the ene reaction. The isoxazolidin-5-yl acetate derivatives are synthons of choice for the preparation of N,O-nucleoside analogues containing purine rings by means of the Vorbruggen protocol. |
| Doi | 10.1055/s-0032-1316916 |
| Wosid | WOS:000319406800015 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | nucleosides; ene reactions; heterocycles; cyclization |