150was added. The aqueous layer was extracted with CH2CI, (3 X 5 mL), and combined CH2C12 layers were washed with 5% aqueous NaHCO, ( I x 10 mL) and H 2 0 (1 X 10 mL), then dried, filtered, and concentrated. Chromatography (9.9:O.l CHCI,/MeOH) afforded 24 (0.019 g, 68%): mp 169-171 OC (EtOAc/ether); IR (CHCI,) ,958,914 cm-I; 'H NMR (60 (s, 6 H), 1.37 (s, 3 H); MS calcd for C14H,,03 (M+-S02Me) 233.1178, found 233.1 155. Procedure for the Conversion of Mercapto Adducts 15 and 20 into Methylthio Adducts 16 and 21, Respectively. Diazabicyclo[5.4.0]undecene (DBU) (1 9 pL, 0.123 mmol) and CH31 (0.1 mL, 1.6 mmol) were added to a solution of the mercapto adduct (0.021 g, 0.0616 mmol) in anhydrous benzene (IO mL). The reaction mixture was stirred for 2 days, then washed with 1 N HCI (3 X IO mL) and H 2 0 ( I X IO mL), dried, filtered, and concentrated to give the corresponding thiomethyl adduct (0.022 g, quantitative yield).Conversion of Amino Adduct 29 into syn-N-Acetylamino Adduct 30. Acetic anhydride (0.5 mL) and pyridine (0.5 mL) were added to a solution of 29 (0.023 g, 0.071 mmol) in CH2C12 (7 mL). The solution was stirred for 23 h, then toluene was added, and the solution was concentrated to give 30 (0.026 g, quantitative yield).Preparation of 0-Acetyl Adduct 28. (Dimethy1amino)pyridine (DMAP) (0.025 g, 0.202 mmol) and acetic anhydride (0.2 mL, 2.0 mmol) were added to a solution of the hydroxy adduct 27 (0.046 g, 0.184 mmol) in anhydrous benzene (8 mL). The solution was refluxed for 3.5 days. Additional 4-(dimethy1amino)pyridine (0.045 g) and acetic anhydride (0.2 mL) were added, and refluxing was continued for 2 more days. TLC showed that the reaction was still incomplete; however, the solution wsa allowed to cool, diluted to 5 mL with EtOAc, washed with 5% (v/v) HCI ( 1 X IO mL) and brine (1 X IO mL), dried, filtered, and concentrated. Chromatography (8:2 petroleum ether/EtOAc) yielded 28 (0.030 g, 52%): mp 136-138 OC (ether); IR (CHCI,)