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The First Synthesis of (4 S ,5 R ,6 R )‐5,6‐Dihydroxy‐4‐(prop‐1‐en‐2‐yl)cyclohex‐1‐ene‐1‐carboxylic Acid
Author(s) -
Ardashov Oleg V.,
Demidova Yuliya S.,
Korchagina Dina V.,
Volcho Konstantin P.,
Simakova Irina L.,
Salakhutdinov Nariman F.
Publication year - 2015
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201500125
Subject(s) - chemistry , yield (engineering) , carboxylic acid , ene reaction , metabolite , terpene , stereochemistry , terpenoid , organic chemistry , biochemistry , materials science , metallurgy
A putative acid metabolite of a novel highly effective antiparkinsonian agent, (4 S ,5 R ,6 R )‐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.