high-resolution mass spectrum caled for Ci2H180g m/e 210.12560, found mje 210.126 05.(±)-(4aa,7a,8a/9)-4, 7,8,[3][4][5][6]pyran-3(4H)-one (20). Phenylselenyl chloride (0.086 g, 0.56 mmol) in dichloromethane (1.0 mL) was added dropwise to a solution of keto alcohol 3b in dichloromethane (2.0 mL) cooled to -78 °C under nitrogen. At the completion of addition, the cooling bath was removed and the light orange solution allowed to warm to room temperature. Removal of solvents and chromatography (silica gel, 10:1 hexanes-EtOAc) afforded the crude selenide which was dissolved in toluene (5 mL) and heated to reflux with tri-n-butyltin hydride (0.22 mL, 0.82 mmol) and a catalytic amount of azobis(isobutyrylnitrile). After 60 min, the solution was cooled to room temperature. Concentration and chromatography (silica gel, 10:1 hexanes-EtOAc) provided ether 20 as a colorless oil: Rt 9.38 min (175 °C, isothermal, 6 ft X 1/i in., 5% SE-30 capillary column gas chromatograph); IR (film 2960, 1725, 1150 cm'1; 100-MHz NMR (CDC13) S 0.98 (d, J = 7 Hz, 3 ), 1.14 (s, 3 HO), 1.3-1.8 (m, 6 ), 2.30 (q, J = 7 Hz, 1 ), 3.60 (m, 1 ), 4.1 (m, 4 H); high-resolution mass spectrum caled for C12H1803 mje 210.12560, found mje 210.12685. Acknowledgment. We thank the National Institutes of Health (Grant No. CA23663) for generous financial assistance.Registry No. 3a (isomer 1), 75233-76-0; 3a (isomer 2), 75233-77-1;