Cyclisation of optically active dihydromyrcenes (2,6-dimethyl-2,7-octadiene): A stereospecific ring contraction

✍ Scribed by H.R. Ansari

• Book ID: 104202987
• Publisher: Elsevier Science
• Year: 1973
• Tongue: French
• Weight: 533 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)83397-4

✦ Synopsis

The isomeric (+) and (-)-dihydromyrcene cychse in organic acids through a stereospecific ring contraction process to give the esters of cw-(S)-(+)-l-(a-hydroxyethyl)-3,3-dimethylcyclohexane and o-(R)-(-)-l-(o-hydroxyethyl)-3,3-dimethylcyclohexane respectively. Small amounts of enantiomeric cis-and trans-tetrahydroeucarvyl esters are also formed. The absolute configuration of the chiral carbinol centres has been determined using Horeau's method. Also, the synthesis of both optical isomers of 3,3-dimethylcyclohexanol has been achieved for the tirst time.