126.22, 126.25, 127.64, 127.96, 128.16, 132.87, 133.17, 137.00,
180.83; m/z (EI) 270.1265 (Mϩ, 22%, C17H18O3 requires
270.1256), 157 (41), 129 (34), 114 (100), 69 (10).
1 H, C(4)H], 3.93–4.16 [m, 3 H, OH ϩ C(5)H2], 5.75 [s, 1 H,
CH(OH)(2-Naph)], 7.40–7.59 (m, 3 H, 1-Naph), 7.72–7.89 (m,
3 H, 1-Naph), 8.12–8.17 (m, 1 H, 1-Naph); δC(67.8 MHz;
CDCl3) 17.49, 32.96, 47.51, 65.84, 71.52, 123.25, 124.92,
125.34, 125.86, 126.02, 128.64, 128.82, 130.91, 133.57, 134.56,
182.14; m/z (EI) 256.1084 (Mϩ, 32%, C16H16O3 requires
256.1100), 157 (80), 129 (53), 100 (100).
trans,erythro-4da. Obtained in admixture with 93% trans,
threo-4da isomers. Viscous oil; readable signals δH(270 MHz,
CDCl3) 1.25 [d, J 2.0, 3 H, C(5)CH3], 1.28–1.39 [m, 1 H,
C(4)H], 1.70–1.74 [m, 1 H, C(4)H], 2.84 (br s, 1 H, OH), 4.52–
4.58 [m, 1 H, C(5)H], 5.04 [s, 1 H, CH(OH)(2-Naph)].
4,5-Dihydro-3-[hydroxy-2-(6-methoxynaphthyl)methyl]-3-
methylfuran-2(3H)-one (threo-4ac). An 87:13 mixture of threo-
4ac and erythro-4ac isomers. White powder, mp 93–96 ЊC
(Found: C, 70.99; H, 6.30. C17H18O4 requires: C, 71.31; H,
6.34%); νmax(KBr)/cmϪ1 3200–3650, 3000–3100, 2800–3000,
1760, 1610, 1490, 1390, 1270, 1030; δH(270 MHz; CDCl3) 1.33
[s, 3 H, C(3)CH3], 1.71 [ddd, J 4.0, 7.3 and 12.9, 1 H, C(4)H],
2.46 [ddd, J 8.2, 8.6 and 12.9, 1 H, C(4)H], 3.90 (s, 3 H, OCH3),
3.98 [ddd, J 4.0, 8.2 and 8.9, 1 H, C(5)H], 4.14 [ddd, J 7.3, 8.6
and 8.9, 1 H, C(5)H], 5.01 [s, 1 H, CH(OH)(6-MeO-2-Naph)],
7.12–7.19 (m, 2 H, 6-MeO-2-Naph), 7.44–7.47 (m, 1 H, 6-MeO-
2-Naph), 7.69–7.77 (m, 3 H, 6-MeO-2-Naph); δC(67.8 MHz;
CDCl3) 17.94, 32.24, 47.50, 55.24, 65.79, 76.66, 105.45, 119.01,
125.32, 125.79, 126.54, 128.30, 129.54, 134.12, 134.27, 157.79,
182.16; m/z (EI) 286.1218 (Mϩ, 21%, C17H18O4 requires
286.1205), 187 (100), 159 (16), 144 (14), 127 (5), 115 (5), 100 (9).
cis,threo-4da. Viscous oil; νmax(liquid film)/cmϪ1 3250–3650,
3000–3100, 2800–3000, 1740, 1200, 1050; δH(270 MHz; CDCl3)
1.31 [s, 3 H, C(3)CH3], 1.40 [d, J 5.9, 3 H, C(5)CH3], 1.72 [dd,
J 5.3 and 12.9, 1 H, C(4)H], 2.01 [dd, J 10.6 and 12.9, 1 H,
C(4)H], 4.51 (br s, 1 H, OH), 4.58 [dqd, J 5.3, 5.9 and 10.6, 1 H,
C(5)H], 5.07 [s, 1 H, CH(OH)(2-Naph)], 7.46–7.52 (m, 3 H,
2-Naph), 7.80–7.87 (m, 4 H, 2-Naph); δC(67.8 MHz; CDCl3)
15.85, 20.79, 41.49, 48.88, 74.70, 77.00, 125.00, 126.06, 126.13,
126.20, 127.58, 127.64, 128.09, 132.90, 133.10, 135.99, 182.46;
m/z (EI) 270.1263 (Mϩ, 26%, C17H18O3 requires 270.1256), 157
(35), 129 (32), 114 (100), 69 (10).
4,5-Dihydro-3-(hydroxy-2-naphthylmethyl)-3-methyl-5-phenyl-
furan-2(3H)-one (trans,threo-4ea). Obtained in admixture with
7% trans,erythro-4ea isomers. White powder, mp 137–139 ЊC
(Found: C, 79.00; H, 6.03. C22H20O3 requires C, 79.40; H,
6.07%): νmax(KBr)/cmϪ1 3150–3600, 3000–3100, 2850–3000,
1760, 1460, 1200; δH(270 MHz; CDCl3) 1.40 [s, 3 H, C(3)CH3],
1.92 [dd, J 8.2 and 13.5, 1 H, C(4)H], 3.01 [dd, J 7.9 and 13.5,
1 H, C(4)H], 3.09 (br s, 1 H, OH), 4.81 [dd, J 7.9 and 8.2, 1 H,
C(5)H], 5.08 [s, 1 H, CH(OH)(2-Naph)], 7.14–7.18 (m, 2 H,
Ph), 7.27–7.35 (m, 3 H, Ph), 7.47–7.59 (m, 3 H, 2-Naph), 7.81–
7.90 (m, 4 H, 2-Naph); δC(67.8 MHz; CDCl3) 21.71, 40.38,
50.15, 65.41, 78.37, 124.60, 124.96, 125.86, 126.02 126.15,
126.33, 126.36, 127.67, 128.09, 128.59, 132.87, 133.24, 136.84,
139.91, 180.54; m/z (EI) 332.1403 (Mϩ, 13%, C22H20O3 requires
332.1413), 176 (100), 157 (28), 131 (37), 107 (8).
erythro-4ac. Viscous oil; readable signals δH(270 MHz;
CDCl3) 1.14 [s, 3 H, C(3)CH3], 1.55–1.64 (m, 1 H), 1.83 (s, 1 H),
2.80–2.97 (m, 1 H), 4.07–4.15 (m, 2 H), 5.05 [s, 1 H, CH(OH)-
(6-MeO-2-Naph)].
4,5-Dihydro-3-[hydroxy(phenyl)methyl]-3-methylfuran-2(3H)-
one (threo-4ad). White powder, mp 78–81 ЊC (Found: C, 69.59;
H, 6.91. C12H14O3 requires: C, 69.89; H, 6.84%); νmax(KBr)/cmϪ1
3200–3700, 3000–3150, 2900–3000, 1770, 1470, 1400, 1210,
1200; δH(270 MHz; CDCl3) 1.31 [s, 3 H, C(3)CH3], 1.71 [ddd,
J 4.1, 7.3 and 13.1, 1 H, C(4)H], 2.43 [ddd, J 8.6, 8.6 and 13.1,
1 H, C(4)H], 3.81 (br s, 1 H, OH), 3.97 [ddd, J 4.1, 8.6 and 8.9,
1 H, C(5)H], 4.10 [ddd, J 7.3, 8.6 and 8.9, 1 H, C(5)H], 4.87
[s, 1 H, CH(OH)Ph], 7.32–7.37 (m, 5 H, Ph); δC(67.8 MHz;
CDCl3) 17.41, 32.40, 47.13, 65.79, 76.62, 126.94, 128.16,
128.28, 138.69, 182.22; m/z (CI) 207.1006 (Mϩ ϩ 1, 1%, C12-
H15O3 requires 207.1021), 189 (1), 107 (29), 100 (100), 79 (19),
56 (10), 41 (12).
trans,erythro-4ea. Obtained in admixture with 3% trans,
threo-4ea isomers. Viscous oil; νmax(liquid film)/cmϪ1 3150–
3600, 3000–3100, 2850–3000, 1760, 1460, 1200; δH(270 MHz;
CDCl3) 1.19 [s, 3 H, C(3)CH3], 1.75 [dd, J 7.9 and 13.5, 1 H,
C(4)H], 2.60 (s, 1 H, OH), 3.20 [dd, J 7.9 and 13.5, 1 H, C(4)H],
5.16 [s, 1 H, CH(OH)(2-Naph)], 5.61 [dd, J 7.9 and 7.9, 1 H,
C(5)H], 7.29–7.40 (m, 5 H, Ph), 7.47–7.55 (m, 3 H, 2-Naph),
7.82–7.92 (m, 4 H, 2-Naph); δC(67.8 MHz; CDCl3) 23.24, 38.21,
50.32, 65.86 78.94, 124.85, 125.10, 126.18, 126.33, 126.40,
126.51, 127.64, 128.07, 128.34, 128.66, 132.92, 133.23, 137.18,
140.56, 181.51; m/z (EI) 332.1408 (Mϩ, 12%, C22H20O3 requires
332.1413), 176 (100), 157 (25), 131 (38), 107 (7).
erythro-4ad. Obtained in admixture with 67% threo-4ad iso-
mer. Viscous oil; δH(270 MHz; CDCl3) 1.12 [s, 3 H, C(3)CH3],
1.61 [ddd, J 4.1, 7.6 and 12.4, 1 H, C(4)H], 1.92 (s, 1 H, OH),
2.80 [ddd, J 8.6, 8.9 and 12.4, 1 H, C(4)H], 4.19 [ddd, J 7.6, 8.9
and 8.9, 1 H, C(5)H], 4.29 [ddd, J 4.1, 8.6 and 8.9, 1 H, C(5)H],
4.92 [s, 1 H, CH(OH)(Ph)], 7.31–7.37 (m, 5 H, Ph).
4,5-Dihydro-3-(hydroxy-4-cyanophenylmethyl)-3-methyl-
furan-2(3H)-one (threo-4ae). An 85:15 mixture of threo-4ae and
erythro-4ae isomers. White powder, mp 93–96 ЊC (Found: C,
67.19; H, 5.81. C13H13NO3 requires: C, 67.52; H, 5.67%);
νmax(KBr)/cmϪ1 3200–3600, 3000–3100, 2850–3000, 2240, 1760,
1620, 1390, 1200, 1100; δH(270 MHz; CDCl3) 1.27 [s, 3 H,
C(3)CH3], 1.57 [ddd, J 3.3, 7.2 and 12.9, 1 H, C(4)H], 2.40 [ddd,
J 8.9, 8.9 and 12.9, 1 H, C(4)H], 4.05 (s, 1 H, OH), 4.08–4.27 [m,
2 H, C(5)H2], 4.94 [s, 1 H, CH(OH)(4-CNC6H4)], 7.46–7.54 (m,
2 H, 4-CNC6H4), 7.63–7.68 (m, 2 H, 4-CNC6H4); δC(67.8 MHz;
CDCl3) 18.19, 31.88, 47.21, 65.72, 75.94, 111.54, 118.40,
127.71, 131.68, 144.51, 181.31.
cis,threo-4ea. White powder, mp 114–115 ЊC; νmax(KBr)/cmϪ1
3150–3600, 3000–3100, 2850–3000, 1760, 1460, 1200; δH(270
MHz; CDCl3) 1.45 [s, 3 H, C(3)CH3], 2.05 [dd, J 5.9 and 12.9,
1 H, C(4)H], 2.37 [dd, J 10.6 and 12.9, 1 H, C(4)H], 4.39 (br s,
1 H, OH), 5.16 [s, 1 H, CH(OH)(2-Naph)], 5.45 [dd, J 5.9 and
10.6, 1 H, C(5)H], 7.21–7.29 (m, 3 H, Ph), 7.30–7.38 (m, 2 H,
Ph), 7.45–7.53 (m, 3 H, 2-Naph), 7.79–7.88 (m, 4 H, 2-Naph);
δC(67.8 MHz; CDCl3) 21.71, 40.36, 50.15, 65.43, 78.37, 124.60,
124.96, 125.86, 126.02, 126.33, 126.36, 127.67, 128.09, 128.14,
128.28, 128.59, 132.87, 136.84, 139.91, 180.54; m/z (EI)
332.1403 (Mϩ, 13%, C22H20O3 requires 332.1413), 176 (100),
157 (23), 131 (39), 107 (8).
erythro-4ae. Viscous oil, readable signals δH(270 MHz;
CDCl3) 1.11 [s, 3 H, C(3)CH3], 1.74 [ddd, J 3.3, 6.9 and 12.9,
1 H, C(4)H], 2.75 [ddd, J 8.9, 8.9 and 12.9, 1 H, C(4)H], 4.08–
4.27 [m, 1 H, C(5)H], 4.35 [ddd, J 3.3, 8.9 and 8.9, 1 H, C(5)H],
4.99 [s, 1 H, CH(OH)(4-CNC6H4)]; δC(67.8 MHz; CDCl3)
20.52, 28.11, 48.72, 65.63, 75.22, 111.54, 118.40, 127.78, 131.75,
145.30, 181.08.
4,5-Dihydro-3-(hydroxy-1-naphthylmethyl)-3-methylfuran-
2(3H)-one (threo-4ab). Viscous oil (Found: C, 74.68; H, 6.27.
C16H16O3 requires: C, 74.98; H, 6.29%); νmax(liquid film)/cmϪ1
3200–3650, 3000–3100, 2850–3000, 1760, 1390, 1210, 1070,
1030; δH(270 MHz; CDCl3) 1.34 [s, 3 H, C(3)CH3], 1.53 [ddd,
J 4.8, 7.3 and 13.2, 1 H, C(4)H], 2.47 [ddd, J 7.9, 8.3 and 13.2,
J. Chem. Soc., Perkin Trans. 1, 1998, 3261–3266
3265