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Reduction with sodium borohydride gave a diastereo-isomeric mixture of alcohols 9;
endo:exo = 9:1, as judged by 1H NMR analysis.
<A NAME="RD02804ST-11">11</A>
Physical Data for SAA 16: 1H NMR (400 MHz, D2O): δ = 4.49 (m, 1 H, H6), 4.09 (d, 1 H, H8, J
8,9 = 5.3 Hz), 4.05 (dd, 1 H, H10, J
10,9 = 5.5 Hz, J
10,1 = 5.9 Hz), 4.02 (m, 2 H, H3ax, H4), 3.89 (dd, 1 H, H9, J
9,8 = 5.3 Hz, J
9,10 = 5.5 Hz), 3.65 (dd, 1 H, H1, J
1,6 = 3.5 Hz, J
1,10 = 5.9 Hz), 3.45 (ddd, 1 H, H3eq, J
3eq,5eq = 1.7 Hz, J
3eq,4 = 7.8 Hz, J
3eq,3ax = 12.4 Hz), 2.37 (m, 1 H, H5ax), 1.86 (m, 1 H, H5eq). 13C NMR (100 MHz, D2O): δ = 177.3 (C=O), 76.8 (C8) 75.2 (C1), 70.9 (C9), 67.6 (C10), 66.7 (C3), 66.0 (C6), 54.9 (C4), 30.7 (C5). ATR-IR (thin film): ν = 3398.1, 2920.0, 2120.1, 1605.6, 1454.5, 1385.0, 1315.5,
1247.7, 1096.9, 1076.7, 1062.2, 1001.4, 947.7, 923.1, 879.9, 811.4 cm-1. MS (ESI): m/z = 260.0 [M + H]+, 282.1 [M + Na]+, 541.1 [2 M + Na]+.
<A NAME="RD02804ST-12">12</A>
Physical Data for SAA 17: 1H NMR (400 MHz, D2O): δ = 4.31 (m, 1 H, H6), 4.10 (d, 1 H, H8, J
8,9 = 5.8 Hz), 4.07 (dd, 1 H, H10, J
10,9 = 6.1 Hz, J
10,1 = 6.3 Hz), 3.83 (dd, 1 H, H9, J
9,8 = 5.8 Hz, J
9,10 = 6.1 Hz), 3.78 (m, 3 H, H3, H4), 3.70 (dd, 1 H, H1, J
1,6 = 3.8 Hz, J
1,10 = 6.3 Hz), 2.15 (m, 2 H, H5). 13C NMR (100 MHz, D2O): δ = 177.4 (C=O), 76.7 (C8) 75.6 (C1), 71.5 (C9), 68.2 (C10), 66.8 (C3, C6), 55.2 (C4), 30.3 (C5). ATR-IR (thin film): ν = 3353.3, 2955.6, 2955.6, 2924.6, 2853.7, 2102.1, 1606.7,
1370.7, 1271.5, 1246.9, 1116.3, 1077.8, 1008.8. 967.4, 941.3 cm-1 MS (ESI): m/z = 260.0 [M + H]+, 282.1 [M + Na]+.