To the crude elimination product obtained above was added 50 mL of 5% potassium hydroxide in methanol. After being stirred for 16 h at room temperature, the mixture was poured into water and extracted with methylene chloride. The combined methylene chloride layers were washed with water and brine, dried, and concentrated. Elution from Florisil (50:50 CHjCl-CsH^) gave oily (±)-vetiselinenol (557 mg, 2.53 mmol, 97% yield), identical in all respects with the IR and NMR spectra of a sample of natural (-)-vetiselinenol:10 IR (neat) 3360 (OH), 1640 (C==C), 890 cm"1 (>C=CH2); NMR (CA) « 0.73 (s, 3 ), 1.01 (d, J = 6 Hz, 3 H), 1.93 (s, 4 ), 1.0-2.6 (complex, 9 H), 3.48 (m, 2 H), 4.67 (br s, 1 H), 4.88 (br s, 1H), 5.37 (br s, 1 H); high-resolution mass spectrum, m/e caled for C14H210 (M -CH3) 205.1592, found 205.1618. Monoacetate 10. In a manner analogous to the preparation of monoacetate 7, methyl lactone 3 (383 mg, 1.64 mmol) was reduced with lithium aluminum hydride to give 385 mg of crude diol 9. This material was acetylated without further purification.The acetylation was carried out as before except that the reaction time was 21 h. Elution of the crude product (497 mg) from Florisil (75:25 CH2C12-C6H12) gave oily monoacetate 10 (251 mg, 0.896 mmol, 55% conversion, 79% yield based on recovered diol 9): IR (neat) 3495 (OH), 1725 (0=0), 1642 (C=C), 1245 (C-O), 885 cm"1 (>C=CH2); NMR (CC14) 0.92 (s, 3 ), 1.02 (d, J = 6 Hz, 3 ), 2.02 (s, 3 ), 4.00 (m, 3 H), 4.47 (br s, 1 H), 4.68 (br s, 1 H); high-resolution mass spectrum, m/e caled for C17H2602 (M -H20) 262.1933, found 262.1920. Further elution of the Florisil column (3:97 EtACACy gave crystalline diol 9 (115 mg, 0.483 mmol). Recrystallization from ether-petroleum ether produced white crystals: mp 113.5-114 °C; IR (KBt) 3175 (OH), 1635 (C=C), 885 cm"1 OOCH^, NMR (CC14) 0.93 (s, 3 ), 0.98 (d,