Formal synthesis of pinolide via L-proline-catalyzed sequential alpha-aminooxylation, horner-wadsworth-emmons olefination and sharpless asymmetric dihydroxylation
| Title | Formal synthesis of pinolide via L-proline-catalyzed sequential alpha-aminooxylation, horner-wadsworth-emmons olefination and sharpless asymmetric dihydroxylation |
| Publication Type | Journal Article |
| Year of Publication | 2016 |
| Authors | Shelke, AM, Suryavanshi, G |
| Journal | Tetrahedron-Asymmetry |
| Volume | 27 |
| Issue | 2-3 |
| Pagination | 142-147 |
| Date Published | FEB |
| ISSN | 0957-4166 |
| Abstract | A convergent, formal enantioselective synthesis of pinolide, a new nonenolide, has been achieved with high enantiomeric purity (99% ee) starting from readily available raw materials. The main highlight of the synthetic strategy is the application of L-proline catalyzed sequential alpha-aminooxylation and Horner-Wadsworth-Emmons olefination of an aldehyde, Sharpless asymmetric dihydroxylation and Steglich esterification as the key steps for the construction of a key chiral intermediate of the target molecule. (C) 2016 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tetasy.2016.01.005 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.108 |
Divison category:
Chemical Engineering & Process Development