The First Synthesis of (4S,5R,6R)-5,6-Dihydroxy-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic Acid

The First Synthesis of (4S,5R,6R)-5,6-Dihydroxy-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic Acid Full article

Journal

Helvetica Chimica Acta
ISSN: 0018-019X , E-ISSN: 1522-2675

Output data

Year: 2015, Volume: 98, Number: 10, Pages: 1442-1455 Pages count : 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	(Данные Web of science) Novosibirsk Organ Chem Inst, RU-630090 Novosibirsk, Russia
2	(Данные Web of science) Novosibirsk State Univ, RU-630090 Novosibirsk, Russia
3	(Данные Web of science) Boreskov Inst Catalysis, RU-630090 Novosibirsk, Russia

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.

Ardashov O.V. , Demidova Y.S. , Korchagina D.V. , Volcho K.P. , Simakova I.L. , Salakhutdinov N.F.
The First Synthesis of (4S,5R,6R)-5,6-Dihydroxy-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic Acid
Helvetica Chimica Acta. 2015. V.98. N10. P.1442-1455. DOI: 10.1002/hlca.201500125 WOS Scopus РИНЦ

Published print:	Oct 1, 2015
Published online:	Oct 13, 2015

Web of science	WOS:000362958200013
Scopus	2-s2.0-84943791180
Elibrary	24960801
OpenAlex	W1945098908