ORDER
REPRINTS
2362
SRIKRISHNA AND DANIELDOSS
(200 MHz, CDCl3): d 6.62 (2 H, s, aromatic H), 6.57 (1 H, d, J ¼ 16.1 Hz),
6.21 (1 H, t of d, J ¼ 16.1 and 6.1 Hz), 4.76 (1 H, t, J ¼ 5.4 Hz, OCHO), 4.28
(2 H, d of AB q, J ¼ 14.5 and 6.1 Hz, OCH2), 3.67 (6 H, s) and 3.64 (3 H, s)
[3 Â ArOCH3], 3.80–3.50 (2 H, m, OCH2CH3), 3.43 (2 H, d, J ¼ 5.4 Hz,
CH2Br), 1.26 (3 H, t, J ¼ 6.6 Hz, OCH2CH3).
Radical cyclisation reaction of the bromoacetal 10c furnished a 3:2
epimeric mixture of the cyclised product 11c in 80% yield. IR (neat): vmax
1
1590, 1510, 1180, 1120 cmꢀ1. H NMR (270 MHz, CDCl3, 3:2 mixture of
diastereomers): d 6.37 and 6.36 (2 H, s), 5.14 (1 H, t, J ¼ 4 Hz), 4.0–3.35 (4 H,
m), 3.84 (6 H, s), 3.81 (3 H, s), 2.70 (2 H, d, J ¼ 7.6 Hz), 2.45 (1 H, m),
1.5–2.3 (2 H, series of multiplets), 1.20 and 1.18 (3 H, t, J ¼ 7 Hz). 13C NMR
(50 MHz, CDCl3, DEPT, 3 : 2 mixture of diastereomers): d 153.1 (2 C), 136.5
(C), 136.3 (C), 105.6 (2 C, CH), 104.3 and 103.8 (CH, O-CH-O), 71.6 (CH2),
62.9 and 62.5 (CH2), 60.6 (CH3), 56.0 (2 C, CH3), 40.1 and 38.8 (CH), 40.2
and 39.5 (CH2), 39.1 and 38.6 (CH2), 15.3 and 15.2 (CH3). Mass: m/z 296
(Mþ, 85%), 250 (50), 207 (25), 182 (40), 181 (50), HRMS: m/z for C16H24O5,
Calcd: 296.1624. Found: 296.1633.
Reaction of the acetal 11c with Jones reagent furnished the lactone 6c
in 70% yield.6 m.p.: 80–82ꢁC (Lit. 79–83ꢁC). IR (neat): vmax 1760,
1
1580 cmꢀ1. H NMR (270 MHz, CDCl3): d 6.35 (2 H, s, aromatic H), 4.34
(1 H, dd, J ¼ 9.2 and 6.9 Hz) and 4.04 (1 H, dd, J ¼ 9.2 and 5.8 Hz) [OCH2],
3.84 (6 H, s, 2 Â m-ArOCH3), 3.82 (3 H, s, p-ArOCH3), 2.87–2.74 (1 H, m,
Ar-CH2CH), 2.7 (2 H, m, Ar-CH2), 2.63 (1 H, dd, J ¼ 17.4 and 8 Hz) and
2.29 (2 H, dd, J ¼ 17.4 and 6.6 Hz) [CH2C ¼ O]. 13C NMR (50 MHz,
CDCl3): d 176.8 (OC ¼ O), 153.3 (2 C, C-30 and 50), 136.7 (C-40), 133.9
(C-10), 105.6 (2 C, C-20 and 60), 72.5 (OCH2), 60.7 (p-ArOCH3), 56.0 (2 C,
2 Â m-Ar-OCH3), 39.2 (ArCH2CH), 37.0 (ArCH2), 34.1 (CH2C ¼ O).
4-[3-Methoxy-(4-phenylmethoxy)phenylmethyl]dihydrofuran-
2-one(6d)
Bromoacetalisation reaction of the alcohol 7d furnished the bromoa-
cetal 10d in 81% yield. IR (neat): vmax 1584, 1503, 1110, 1023 cmꢀ1
.
1H NMR (90 MHz, CDCl3): d 7.45–7.25 (5 H, m), 6.95 (1 H, s), 6.8 (2 H,
s), 6.6 (1 H, d, J ¼ 17 Hz), 6.16 (1 H, t of d, J ¼ 17 and 6 Hz), 5.15 (2 H, s),
4.75 (1 H, t, J ¼ 5.4 Hz), 4.28 (2H, d, J ¼ 6 Hz), 3.9 (3 H, s), 3.65 (2 H, m),
3.41 (2 H, d, J ¼ 5.4 Hz), 1.25 (3 H, t, J ¼ 7.5 Hz). 13C NMR (22.5 MHz,
CHCl3): d 149.3, 147.8, 136.7, 132.3, 129.8, 128.2 (2 C), 127.5, 126.9 (2 C),
123.0, 119.4, 113.5, 109.2, 100.5, 70.6, 67.1, 62.1, 55.6, 31.5, 14.9. Mass: m/z
421 (Mþ þ 1, 25%), 419 (25), 269 (25), 253 (25), 179 (40), 153 (25), 151 (25),
125 (20), 123 (20), 91 (100).