General approach to medium-sized ring ethers via hydrolytic and oxidative kinetic resolutions: stereoselective syntheses of (-)-cis-lauthisan and (+)-isolaurepan
| Title | General approach to medium-sized ring ethers via hydrolytic and oxidative kinetic resolutions: stereoselective syntheses of (-)-cis-lauthisan and (+)-isolaurepan |
| Publication Type | Journal Article |
| Year of Publication | 2009 |
| Authors | Tripathi, D, Pandey, SKumar, Kumar, P |
| Journal | Tetrahedron |
| Volume | 65 |
| Issue | 11 |
| Pagination | 2226-2231 |
| Date Published | MAR |
| ISSN | 0040-4020 |
| Keywords | cis-Reductive cyclization, Jacobson's Hydrolytic Kinetic Resolution (HKR), Oxepanes, Oxidative resolution of secondary alcohol, Ring ether |
| Abstract | A short and enantioselective approach to medium ring ethers and its application to the syntheses of (-)-cis-lauthisan and (+)-isolaurepan are described. The synthetic strategy features Jacobson's Hydrolytic Kinetic Resolution (HKR), oxidative resolution of secondary alcohol, and highly diastereoselective Et(3)SiH/TMSOTf-promoted reductive cyclization of a hydroxy ketone to give exclusively the different medium-sized cis-disubstituted cyclic ethers. (C) 2009 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tet.2009.01.062 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.011 |
Divison category:
Organic Chemistry