The First Synthesis of (4S,5R,6R)‐5,6‐Dihydroxy‐4‐(prop‐1‐en‐2‐yl)cyclohex‐1‐ene‐1‐carboxylic Acid |
| |
| Authors: | Oleg V Ardashov Yuliya S Demidova Dina V Korchagina Konstantin P Volcho Irina L Simakova Nariman F Salakhutdinov |
| |
| Institution: | 1. Novosibirsk Institute of Organic Chemistry, pr. Lavrentieva, 9, RU‐630090 Novosibirsk, (phone: +7‐383‐3308870;2. fax: +7‐383‐3309752);3. Novosibirsk State University, Pirogova 2, RU‐630090 Novosibirsk;4. Boreskov Institute of Catalysis, pr. Lavrentieva, 5, RU‐630090 Novosibirsk |
| |
| Abstract: | A putative acid metabolite of a novel highly effective antiparkinsonian agent, (4S,5R,6R)‐5,6‐dihydroxy‐4‐(prop‐1‐en‐2‐yl)cyclohex‐1‐ene‐1‐carboxylic acid ( 5 ), was synthesized for the first time. Several synthetic approaches based on different transformations of O‐bearing monoterpenoids of the pinane and p‐menthane series were developed and tested in the course of the study. Acid 5 was synthesized starting from a commercially available monoterpenoid, (?)‐verbenone, in a total yield of 4.4% over eight steps. |
| |
| Keywords: | Acid metabolites Antiparkinsonian activity Isomerization Monoterpenoids Oxidation |
|
|
