Helvetica Chimica Acta – Vol. 98 (2015)
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J ¼ 8.5, 1 H); 7.71 (dd, J ¼ 7.2, 1.1, 1 H); 7.63 – 7.51 (m, 3 H); 5.04 (d, J ¼ 2.8, 1 H); 4.13 – 4.09 (m, 1 H);
3.77 (br. s, OH); 1.80 (br. s, OH); 1.65 – 1.61 (m, 2 H); 1.42 – 1.21 (m, 6 H); 0.85 (t, J ¼ 6.8, 3 H). 13C-NMR
(100 MHz, CDCl3): 204.1; 134.0; 133.2; 132.9; 130.3; 128.4; 128.2; 126.92; 126.87; 125.5; 124.2; 77.3; 72.8;
34.7; 31.6; 25.4; 22.5; 14.0. HR-ESI-MS: 309.1464 (C18H22NaOþ3 ; calc. 309.1461).
Data of 9c. IR (CHCl3): 3429, 3013, 2930, 2858, 1598, 1513, 1456, 1261, 1124, 1058, 872, 669. 1H-NMR
(400 MHz, CDCl3; mixture of diastereoisomers, ca. 2 :1): 8.08 (d, J ¼ 7.9, 1 H); 7.99 – 7.95 (m, 1 H); 7.89 –
7.86 (m, 2 H); 7.84 (d, J ¼ 7.1, 2 H); 7.74 (d, J ¼ 7.2, 1 H); 7.68 (d, J ¼ 7.0, 2 H); 7.54 – 7.46 (m, 5 H); 5.80 –
5.78 (m, 1 H); 5.61 (d, J ¼ 4.6, 1 H); 3.82 – 3.75 (m, 3 H); 3.59 – 3.57 (m, 1 H); 1.59 – 1.50 (m, 4 H); 1.33 –
1.03 (m, 12 H); 0.88 (t, J ¼ 6.7, 3 H); 0.83 (t, J ¼ 6.9, 3 H). 13C-NMR (100 MHz, CDCl3): 136.3; 136.1;
133.8; 133.6; 130.65; 130.1; 129.0; 128.5; 128.3; 126.4; 126.3; 125.7; 125.6; 125.43; 125.4; 124.6; 123.5;
122.9; 122.7; 75.6; 74.9; 74.0; 72.4; 72.2; 70.2; 34.3; 33.8; 31.6; 31.5; 25.3; 25.1; 22.5; 22.4; 14.0; 13.9. HR-
ESI-MS: 311.1618 (C18H24NaOþ3 ; 311.1618).
2,3-Dihydroxy-1-phenyloctan-1-one (8d) and 1-Phenyloctane-1,2,3-triol (9d). From 6d (50 mg,
0.245 mmol) by GP 2. Yield: 26 mg (45%) of 8d and 18.1 mg (31%) of 9d. Colorless oils.
Data of 8d [8b]. IR (CHCl3): 3432, 3020, 2927, 2856, 1695, 1451, 1416, 1318, 1267, 1177, 1071, 981, 911,
713, 668. 1H-NMR (400 MHz, CDCl3): 7.89 (dd, J ¼ 8.5, 1.3, 2 H); 7.63 – 7.61 (m, 1 H); 7.53 – 7.50 (m, 2 H);
5.01 – 4.98 (m, 1 H); 3.94 – 3.92 (m, 2 H); 1.73 (br. s, OH); 1.72 – 1.66 (m, 2 H); 1.52 – 1.24 (m, 6 H); 0.90
(t, J ¼ 6.9, 3 H). 13C-NMR (100 MHz, CDCl3): 200.3; 134.0; 133.7; 128.9; 128.5; 75.4; 72.9; 34.7; 31.7; 25.5;
22.6; 14.0. HR-ESI-MS: 259.1307 (C14H20NaOþ3 ; calc. 259.1305).
Data of 9d. IR (CHCl3): 3412, 3032, 2955, 2931, 2860, 1653, 1495, 1455, 1134, 1061, 917, 841, 702, 670.
1H-NMR (400 MHz, CDCl3; mixture of diastereoisomers, ca. 1:1): 7.41 – 7.28 (m, 10 H); 4.95 (d, J ¼ 4.5,
1 H); 4.81 (d, J ¼ 5.6, 1 H); 3.77 – 3.52 (m, 4 H); 1.61 – 1.15 (m, 22 H); 0.90 – 0.84 (m, 6 H). 13C-NMR
(100 MHz, CDCl3): 140.7; 140.6; 128.6; 128.56; 128.1; 127.8; 126.7; 126.0; 77.2; 76.9; 75.7; 75.4; 71.8; 70.2;
34.3; 33.8; 31.7; 31.6; 25.24; 25.2; 22.5; 14.0. HR-ESI-MS: 261.1461 (C14H22NaOþ3 ; calc. 261.1461).
2,3-Dihydroxy-1-phenylheptan-1-one (8e) and 1-Phenylheptane-1,2,3-triol (9e). From 6e (100 mg,
0.525 mmol) by GP 2. Yield: 49.0 mg (42%) of 8e and 37.7 mg (32%) of 9e. Colorless oils.
Data of 8e [7]. IR (CHCl3): 3451, 3064, 3014, 2957, 2932, 2861, 1683, 1599, 1580, 1450, 1404, 1305,
1269, 1240, 1133, 1089, 1002, 978, 854, 691. 1H-NMR (400 MHz, CDCl3/TMS): 7.89 (dd, J ¼ 8.5, 1.3, 2 H);
7.65 – 7.61 (m, 1 H); 7.53 – 7.50 (m, 2 H); 5.01 (dd, J ¼ 5.5, 1.4, 1 H); 3.97 – 3.93 (m, 2 H); 1.85 – 1.82 (m,
OH); 1.77 – 1.72 (m, 2 H); 1.54 – 1.32 (m, 4 H); 0.93 (t, J ¼ 7.1, 3 H ) . 13C-NMR (100 MHz, CDCl3): 200.3;
133.9; 133.7; 128.9; 128.4; 75.4; 72.9; 34.3; 27.9; 22.6; 14.0. HR-ESI-MS: 245.1153 (C13H18NaOþ3 ; calc.
245.1148).
Data of 9e [18]. IR (CHCl3): 3392, 3062, 3031, 2955, 2931, 2871, 2857, 1636, 1493, 1466, 1454, 1324,
1270, 1198, 1130, 1052, 1021, 913, 849, 869, 794, 702. 1H-NMR (400 MHz, CDCl3; mixture of
diastereoisomers, ca. 2 :1): 7.38 – 7.27 (m, 10 H); 4.92 (d, J ¼ 4.1, 1 H); 4.77 (d, J ¼ 5.9, 1 H); 4.00 – 3.98
(br. s, OH); 3.70 – 3.62 (m, 2 H); 3.55 – 3.46 (m, 3 H); 3.28 – 3.13 (m, 2 H); 2.70 – 2.68 (m, OH); 2.07 – 2.04
(m, OH); 1.58 – 1.39 (m, 4 H); 1.38 – 1.19 (m, 8 H); 0.92 – 0.81 (m, 6 H). 13C-NMR (100 MHz, CDCl3):
140.8; 140.7; 128.4; 127.9; 127.6; 126.7; 126.0; 76.9; 76.6; 75.5; 71.5; 70.2; 33.9; 33.3; 27.7; 27.6; 22.53; 22.5;
13.9. HR-ESI-MS: 247.1304 (C13H20NaOþ3 ; calc. 247.1305).
2,3-Dihydroxy-1-(2-methoxyphenyl)octan-1-one (8f) and 1-(2-Methoxyphenyl)octane-1,2,3-triol
(9f). From 6f (50 mg, 0.213 mmol) by GP 2. Yield: 21.6 mg (38%) of 8f and 18.9 mg (33%) of 9f.
Colorless oils.
Data of 8f [8c]. IR (CHCl3): 3445, 2930, 2858, 1668, 1560, 1487, 1469, 1293, 1247, 1165, 1135, 1090,
1
1021, 985, 646. H-NMR (400 MHz, CDCl3/TMS): 7.86 (dd, J ¼ 7.8, 1.8, 1 H); 7.54 (td, J ¼ 7.8, 1.8, 1 H);
7.09 – 7.05 (m, 1 H); 6.99 (d, J ¼ 8.4, 1 H); 5.06 (d, J ¼ 0.8, 1 H); 4.12 (br. s, OH); 3.91 (s, 3 H); 3.88 – 3.83
(m, 1 H); 1.79 (br. s, OH); 1.73 – 1.64 (m, 2 H); 1.52 – 1.25 (m, 6 H); 0.90 (t, J ¼ 6.9, 3 H). 13C-NMR
(100 MHz, CDCl3): 201.6; 158.5; 134.9; 131.6; 123.9; 121.4; 111.4; 78.7; 71.8; 55.4; 35.2; 31.7; 25.5; 22.6;
14.0. HR-ESI-MS: 289.1417 (C15H22NaOþ4 ; calc. 289.1410).
Data of 9f. IR (CHCl3): 3410, 2932, 2859, 1677, 1603, 1589, 1492, 1465, 1439, 1289, 1241, 1136, 1051,
1
1029, 938, 838. H-NMR (400 MHz, CDCl3; mixture of diastereoisomers, ca. 2 :1): 7.47 – 7.42 (m, 2 H);
7.31 – 7.26 (m, 2 H); 7.03 – 6.99 (m, 2 H); 6.92 – 6.87 (m, 2 H); 5.20 (d, J ¼ 4.5, 1 H); 5.00 (d, J ¼ 6.0, 1 H);
3.86 (s, 3 H); 3.83 (s, 3 H); 3.76 – 3.73 (m, 2 H); 3.57 (dd, J ¼ 6.1, 2.0, 2 H), 3.50 – 3.46 (m, 2 H); 2.62 (br. s,
4 OH); 1.61 – 1.16 (m, 16 H); 0.90 – 0.82 (m, 6 H). 13C-NMR (100 MHz, CDCl3): 156.3; 156.0; 128.9;