[Si](OC[CH2:10][C:11]([CH2:21]C=C)([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:12]#[N:13])(C(C)(C)C)(C)C.ClCCl.[Mn]([O-])(=O)(=O)=O.[K+].S([O-])([O-])=O.[Na+].[Na+].[C:39]([OH:42])(=[O:41])[CH3:40]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[O-2].[O-2].[Mn+4].C(OCC)(=O)C.CCCCCC.O>[C:12]([C:11]1([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:21][O:42][C:39](=[O:41])[CH2:40][CH2:10]1)#[N:13]
Combine 2-(2-(t-butyldimethylsilyloxy)ethyl)-2-allyl-3-phenylpropionitrile (1.19 g) and dichloromethane (25 mL) and water (25 mL). Add tetrabutyl ammonium bromide (0.01 g) and acetic acid (8.0 mL). Add potassium permanganate (2.24 g) portionwise over 2 hours. After 18 hours, add sodium sulfite to dissolve the precipitated manganese dioxide. Separate the layers and adjust the pH of the aqueous layer to about 2 using aqueous 1 M hydrochloric acid solution. Extract the aqueous layer three times with dichloromethane. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 1/1 ethyl acetate/hexane to give 4-cyano-4-phenylmethyl-δ-valerolactone.
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