The First Synthesis of (4S,5R,6R)-5,6-Dihydroxy-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic Acid
Full article
| Общее |
Language:
Английский,
Genre:
Full article,
Status:
Published,
Source type:
Original
|
| Journal |
Helvetica Chimica Acta
ISSN: 0018-019X
, E-ISSN: 1522-2675
|
| Output data |
Year: 2015,
Volume: 98,
Number: 10,
Pages: 1442-1455
Pages count
: 4
DOI:
10.1002/hlca.201500125
|
| Tags |
Acid metabolites, Antiparkinsonian activity, Isomerization, Monoterpenoids, Oxidation |
| Authors |
Ardashov Oleg V.
1,2
,
Demidova Yuliya S.
2,3
,
Korchagina Dina V.
1
,
Volcho Konstantin P.
1,2
,
Simakova Irina L.
2,3
,
Salakhutdinov Nariman F.
1,2
|
| Affiliations |
| 1 |
Novosibirsk Institute of Organic Chemistry, pr. Lavrentieva, 9, RU-630090 Novosibirsk
|
| 2 |
Novosibirsk State University, Pirogova 2, RU-630090 Novosibirsk
|
| 3 |
Boreskov Institute of Catalysis, pr. Lavrentieva, 5, RU-630090 Novosibirsk
|
|
Funding (1)
|
1
|
Federal Agency for Scientific Organizations
|
V.46.4.4.
|
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.