Enantioselective synthesis of natural (−)-tochuinyl acetate, (−)-dihydrotochuinyl acetate and (+)-β-cuparenone using both enantiomers of the same building block |
| |
Authors: | Samir Acherar |
| |
Affiliation: | Laboratoire de Réactivité Organique Sélective, U.M.R. 6180 “Chirotechnologies: catalyse et biocatalyse”, Faculté des Sciences et Techniques de St Jérôme, 13397 Marseille cedex 20, France |
| |
Abstract: | The first enantioselective synthesis of tochuinyl acetate and dihydrotochuinyl acetate, two natural marine products isolated from Tochuina tetraquetra and Gersemia rubiformis, has been achieved starting from an enantiopure building block. The key feature of the present synthesis is complete control of two vicinal quaternary stereogenic centers present in the natural products and elucidation of their absolute stereochemistry, which was previously unknown. Furthermore, starting from the enantiomer of the same building block, the applied methodology provided a new approach towards natural (R)-(+)-β-cuparenone. |
| |
Keywords: | Total synthesis Configuration determination Enantioselectivity Cuparane family Lipases |
本文献已被 ScienceDirect 等数据库收录! |
|