113084-12-1Relevant articles and documents
Synthesis and Absolute Stereochemistry of Chiral γ-Ionone and Dihydro-γ-ionone
Oritani, Takayuki,Yamashita, Kyohei
, p. 1271 - 1276 (2007/10/02)
The optical resolution of (+/-)-α-cyclogeranic acid (4) with (-)-α-methylbenzylamine gave (-)-(S)-α-cyclogeranic acid (4).Epoxidation of (-)-(S)-methyl α-cyclogeranate (5), followed by reduction with lithium aluminium hydride, gave mainly (-)-(1R,2R)-2-hydroxy-2,6,6-trimethyl-1-cyclohexanemethanol (7b), which was oxidized with pyridinium chlorochromate to give (-)-hydroxyaldehyde 8.The reaction of aldehyde 8 with 2-oxopropylidenetriphenylphosphorane gave (-)-(1'S,2'R)-2',3'-dihydro-2'-hydroxy-α-ionone (9).The thermal decomposition of (1'S)-2'-acetoxy-2',3'-dihydro-α-ionone (10) gave (-)-(S)-α-ionone (2) and (+)-(S)-γ-ionone (1).The partial hydrogenation of (+)-(S)-γ-ionone (1) gave (+)-(S)-dihydro-γ-ionone (3).