|
|||||
|
|
Synthesis of a lactone natural product found in Greek tobacco |
|
| Authors: | J Stephen Clark Stewart T Hayes Luca Gobbi |
| Institution: | a WestCHEM, Department of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ, UK b School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK c F. Hoffmann-La Roche Ltd, Pharmaceuticals Division, Bldg. Discovery Chemistry, CH-4070 Basel, Switzerland |
| Abstract: | A short and stereoselective synthesis of (3R∗,4R∗,7R∗)-3,7-epoxy-4,8-dimethyl-8-nonen-4-olide, a natural product isolated from cured tobacco leaves, has been completed in six steps and 22% overall yield. A samarium(II) iodide mediated reductive cyclisation has been used to construct the functionalised tetrahydropyranol core and subsequent sequential stereoselective addition of methyllithium and lactonisation furnished the natural product. |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ | |