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12 A solution of 632 mg (2.00 mmol) of alkene 2 and 1.00 g of potassium acetate in 10 mL of HOAc was heated to 90 °C under argon atmosphere. After the addition of 2.14 g (8.00 mmol, 4.0 equiv) of manganese(III) acetate dihydrate, the solution was stirred at this temperature for 60 h. The mixture was diluted with 300 mL of ice water, extracted with 8 × 50 mL of CH2Cl2 and the combined organic phases were washed with 100 mL of a diluted solution of Na2S2O3 and 4 × 50 mL of a solution of NaHCO3 and dried over Na2SO4. The solvent was removed at 35 °C and the residue was purified by silica gel column chromatography (CH2Cl2-EtOAc 90:10) to afford 455 mg (61%) of manno-5 (R
f
= 0.27) as a white solid, mp 129-130 °C (recrystalliza-tion from EtOH) and 220 mg (29%) of gluco-5 (R
f
= 0.22) as a colorless oil. Lactone manno-5: [α]D
25 +10.5 (c 1.01, CHCl3). 1H NMR (500 MHz, CDCl3): δ = 2.07, 2.08, 2.12, 2.14 (4 s, each 3 H, OAc), 2.17 (dddd, J = 13.2, 9.8, 9.0, 7.4 Hz, 1 H, 3-H), 2.24 (dddd, J = 13.2, 9.0, 7.4, 5.5 Hz, 1 H, 3′-H), 2.51 (dt, J = 17.9, 9.0 Hz, 1 H, 2-H), 2.57 (ddd, J = 17.9, 9.8, 5.5 Hz, 1 H, 2′-H), 4.13 (dd, J = 12.5, 4.8 Hz, 1 H, 8-H), 4.26 (dd, J = 12.5, 2.7 Hz, 1 H, 8′-H), 4.57 (dt, J = 7.4, 6.1 Hz, 1 H, 4-H), 5.08 (ddd, J = 8.7, 4.8, 2.7 Hz, 1 H, 7-H), 5.33 (dd, J = 6.1, 2.5 Hz, 1 H, 5-H), 5.51 (dd, J = 8.7, 2.5 Hz, 1 H, 6-H). 13C NMR (125 MHz, CDCl3): δ = 20.6, 20.7, 20.8, 20.9 (4 q, OAc), 23.4 (t, C-3), 27.7 (t, C-2), 61.5 (t, C-8), 68.0, 68.1, 69.9 (3 d, C-5, C-6, C-7), 77.2 (d, C-4), 169.5, 169.9, 170.0, 170.6 (4 s, OAc), 176.1 (s, C-1). Anal. Calcd for C16H22O10: C, 51.34; H, 5.92. Found: C, 51.18; H, 5.84. Lactone gluco-5: [α]D
25 +36.0 (c 1.15, CHCl3). 1H NMR (500 MHz, CDCl3): δ = 2.01 (dddd, J = 13.2, 9.1, 8.9, 7.2 Hz, 1 H, 3-H), 2.04, 2.06, 2.11, 2.14 (4 s, each 3 H, OAc), 2.34-2.42 (m, 1 H, 3′-H), 2.46-2.50 (m, 2 H, 2-H), 4.14 (dd, J = 12.6, 4.3 Hz, 1 H, 8-H), 4.22 (dd, J = 12.6, 2.5 Hz, 1 H, 8′-H), 4.57 (td, J = 7.2, 5.5 Hz, 1 H, 4-H), 5.10 (ddd, J = 9.1, 4.3, 2.5 Hz, 1 H, 7-H), 5.25 (dd, J = 5.5, 2.2 Hz, 1 H, 5-H), 5.42 (dd, J = 9.1, 2.2 Hz, 1 H, 6-H). 13C NMR (125 MHz, CDCl3): δ = 20.6, 20.7, 20.8, 20.9 (4 q, OAc), 24.4 (t, C-3), 27.7 (t, C-2), 61.4 (t, C-8), 67.8, 68.2, 70.6 (3 d, C-5, C-6, C-7), 78.4 (d, C-4), 169.7, 170.1, 170.2, 170.5 (4 s, OAc), 175.7 (s, C-1). Anal. Calcd for C16H22O10: C, 51.34; H, 5.92. Found: C, 51.37; H, 5.72.
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