A practical synthesis of (+/-)-alpha-isosparteine from a tetraoxobispidine core
Blakemore, PR; Kilner, C; Norcross, NR; Astles, PC
| HERO ID | 4923626 |
|---|---|
| In Press | No |
| Year | 2005 |
| Title | A practical synthesis of (+/-)-alpha-isosparteine from a tetraoxobispidine core |
| Authors | Blakemore, PR; Kilner, C; Norcross, NR; Astles, PC |
| Journal | Organic Letters |
| Volume | 7 |
| Issue | 21 |
| Page Numbers | 4721-4724 |
| Abstract | [reaction: see text] The title alkaloid was synthesized in racemic form from 3,7-diallyl-2,4,6,8-tetraoxo-3,7-diazabicyclo[3.3.1]nonane (7) by a regioselective diallylation reaction followed by double ring-closing olefin metathesis and exhaustive reduction. Tetraoxobispidine 7 was itself prepared in three simple operations from dimethyl malonate. The entire sequence to alpha-isosparteine was conducted on a multigram scale and proceeded without recourse to chromatography. |
| Doi | 10.1021/ol0519184 |
| Pmid | 16209519 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |