J. Org. Chem. 1985, 50, 936-940
936
of NaI04 (1.39 g, 6.5 mmol) in water (30 mL) was added portionwise to a stirrd solution of the diol 29 (1.20 g, 6.5 mmol) in dilute MeOH (H,O:MeOH, 3:5,80 mL) at 0 "C, and the mixture was stirred for 5 min at 0 "C. To this mixture was added NaBH, (0.24 g, 6.5 mmol) portionwise at the same temperature, and the reaction was quenched with 6 N HCl. The mixture was extracted with CHZC12and the extract was washed with brine, dried (MgSO4), and concentrated. The residue was chromatographed on silica gel (40 g) by using Et0Ac:n-hexane (1:B) as eluent to give the primary alcohol 31 (0.81 g, 80.9%): bp (Kugelrohr) -120 "C (350 mmHg); [U]D -67.81' (c 2.908, CHC13);IR (film) 3350, 3080, 1645 cm-'; MS, m/e (relative intensity) 154 (M+),109 (100); 'H NMR 6 1.43 (br, 1 H, disappeared with D,O, -OH), 1.67 (d, 3 H, J = 1 Hz, =C(CH3)-), 1.7 (br s , 6 H, =C(CH,),), 1.53-2.1 (m, 2 H, -CH2CH2CH
