SYNTHESIS OF ENANTIOMERIC CIS-HOMOCARONIC ACIDS FROM (-3-CARENE())

Authors
MAKAEV FZ GALIN FZ TOLSTIKOV GA
Citation
Fz. Makaev et al., SYNTHESIS OF ENANTIOMERIC CIS-HOMOCARONIC ACIDS FROM (-3-CARENE()), Russian chemical bulletin, 44(2), 1995, pp. 305-309
Citations number
20
Categorie Soggetti
Chemistry
Journal title
Russian chemical bulletin → ACNP
ISSN journal
10665285
Volume
44
Issue
2
Year of publication
1995
Pages
305 - 309
Database
ISI
SICI code
1066-5285(1995)44:2<305:SOECAF>2.0.ZU;2-7
Abstract
The syntheses of the dimethyl ester of (-)-(1R)-cis-homocaronic acid ( 7 steps, overall yield 43 %) and its antipode, the dimethyl ester of ( +)-(1S)-cis-homocaronic acid (5 steps, overall yield 27 %), were perfo rmed starting from (+)-3-carene and its derivatives, (+)-4 alpha-acety l-2-carene and (+)-4 alpha-acetoxymethyl-2-carene. Oxidative cleavage in the key stages was carried out by ozonization.