and concentrated in vacuo to afford a crude mixture of two epoxides 9 73 g chromatography silica gel 60 1000 g with et 3 n hexane 1 19 to 1 9 as eluent afforded 3s 4s trans 3 4 epoxy 1 phenyl 8 2 tetrahydropyranyloxy 1 z octene 5 16 g 52 as a clear colorless oil analysis calculated for c 19 h 26 o 3 c 75 46 h 8 67 found c 75 38 h 8 61 further elution afforded 3s 4s trans 3 4 epoxy 1 phenyl 8 2 tetrahydropyranyloxy 1 e octene 2 84 g 29 as a clear colorless oil analysis calculated for c 19 h 26 o 3 c 75 46 h 8 67 found c 75 51 h 8 77 g thiophenol 2 34 ml 22 82 mm ch 3 oh 75 ml and triethylamine 6 36 ml 45 63 mm were added sequentially to the e epoxide product of example 1f 2 30 g 7 61 mm under n 2 after stirring overnight the reaction mixture was concentrated in vacuo to afford crude 3r 4s 4 hydroxy 1 phenyl 3 phenylthio 8 2 tetrahydropyranyloxy 1 e octene 4 69 g as a clear yellow oil chromatography silica gel 60 70 230 mesh 500 g with et 3 n etoac hexane 1 2 17 to.