[OH:1][C:2]([CH3:21])([CH3:20])[C:3]#[C:4][CH2:5][C@H:6]([C:8]1[C@:9]2([CH3:19])[C@@H:14]([CH2:15][CH2:16][CH:17]=1)[C@@H:13]([OH:18])[CH2:12][CH2:11][CH2:10]2)[CH3:7].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[OH:1][C:2]([CH3:20])([CH3:21])[C:3]#[C:4][CH2:5][C@H:6]([C:8]1[C@:9]2([CH3:19])[C@@H:14]([CH2:15][CH2:16][CH:17]=1)[C:13](=[O:18])[CH2:12][CH2:11][CH2:10]2)[CH3:7]590 mg (2.03 mmol) of (1S,4aS,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hex-3-ynyl]-4a-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol was dissolved in 10 ml of abs. CH2Cl2 and oxidized with 1.91 g (5.08 mmol) of pyridinium dichromate during 2 h at ambient temperature. Filtration over Celite, evaporation to dryness, and flash chromatography (SiO2, Hexane/AcOEt=7/3) produced 446 mg of the title compound as colorless oil.
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