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(O)CH]CH), 6.13 (dd, J¼5.2, 1.6 Hz, 1H, CH]CHC(O)CH]CH), 6.29
(t, J¼3.6 Hz, 1H, HOCH2C]CH), 7.02 (dd, J¼20.6, 4.0 Hz, 1H, CH]
CHC(O)CH]CH), 7.03 (dd, J¼7.2, 4.0 Hz, 1H, CH]CHC(O)CH]CH);
13C NMR (100 MHz, CDCl3)
d 35.7 (CCH2CH2C), 36.0 (CCH2CH2C),
61.5 (CH2OH), 68.1 (OCH2C]O), 80.8 (CCH2CH2CO), 107.2
(CCH2CH2CO), 124.0 (HOCH2C]CH), 128.0 (CH]CHC(O)CH]CH),
128.4 (CH]CHC(O)CH]CH), 150.6 (CH]CHC(O)CH]CH), 152.8
(CH]CHC(O)CH]CH), 162.0 (HOCH2C]CH), 187.3 (CH]CHC(O)
CH]CH), 196.8 (C]CHC]O); MS (ESIþ) m/z (%) 285 [MþNa]þ
(100), 263 (16%), 264 (2%); HRMS (ESIþ) m/z found 285.0733.
C14H14O5Na requires 285.0736.
6.3.7. (ꢀ)-2-[(5,6-Dihydro-5-oxo-2H-pyran-3-yl)methyl tetradeca-
noate]-1-oxaspiro[4.5]deca-6,9-dien-8-one ((þ/ꢂ)-49). To a solu-
tion of 48 (34.6 mg, 0.13 mmol) in dry CH2Cl2 (2 mL) were added at
0 ꢁC DMAP (16.1 mg, 0.13 mmol), myristol chloride (42.4 mg,
0.17 mmol) and Et3N (17.3 mg, 0.17 mmol). After 30 min at 0 ꢁC and
2 h at rt, an aqueous solution of HCl 1 N was added. The product
was extracted with CH2Cl2, dried over MgSO4 and concentrated.
The residue was subjected to silica gel column chromatography
(cyclohexane/EtOAc 70:30) to give 49 (23.5 mg, 38%); Rf
(cyclohexane/EtOAc 7:3) 0.18; IR nmax (film, cmꢂ1) 2914, 2845, 1752,
1683, 1469, 1275, 1251, 1162, 1025, 1013, 900, 847; UV
(MeOH) 221 nm; 1H NMR (400 MHz, CDCl3)
d
0.88 (t,
6. Peuchmaur, M.; Saidani, N.; Botté, C.; Maréchal, E.; Vial, H.; Wong, Y.-S. J. Med.
J¼6.8 Hz, 3H, CH3(CH2)10CH2CH2C]O), 1.26e1.28 (m, 20H,
CH3(CH2)10CH2CH2C]O), 1.67e1.75 (m, 2H, CH3(CH2)10CH2CH2C]
O), 2.19e2.29 (m, 2H, CCH2CH2C), 2.23e2.38 (m, 2H, CCH2CH2C),
2.52e2.60 (CH3(CH2)10CH2CH2C]O), 4.18 (d, J¼16.8 Hz, 1H, OCH-
HaC]O), 4.51 (d, J¼16.8 Hz, 1H, OCHHbC]O), 4.72 (dd, J¼20.0,
1.6 Hz, 1H, CH]CCHHaOC]O), 4.91 (dd, J¼1.6 Hz, 1H, CH]
CCHHbOC]O), 6.19 (dd, J¼11.6, 2.0 Hz, 1H, CH]CHC(O)CH]CH),
6.22 (dd, J¼11.6, 2.0 Hz, 1H, CH]CHC(O)CH]CH), 6.25 (t, J¼1.6 Hz,
1H, CH]CCH2OC]O), 6.80 (dd, J¼10.0, 3.2 Hz, 1H, CH]CHC(O)
CH]CH), 6.89 (dd, J¼10.0, 3.2 Hz, 1H, CH]CHC(O)CH]CH); 13C
Chem. 2008, 51, 4870e4873.
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NMR (100 MHz, CDCl3)
d
14.3 (CH3CH2CH2(CH2)8), 22.9
(CH3CH2CH2(CH2)8), 25.0 (CH3CH2CH2(CH2)8CH2CH2C]O), 29.2
(CH3CH2CH2(CH2)8), 30.1 (CH3CH2CH2(CH2)8CH2CH2C]O), 61.7
(CH]CCH2OC]O), 67.0 (OCH2C]O), 79.7 (CCH2CH2CO), 105.9
(OCCH2CH2CO), 125.4 (CH]CCH2OC]O), 128.0 (CH]CHC(O)CH]
CH), 147.2 (CH]CHC(O)CH]CH), 149.7 (CH]CCH2OC]O), 173.3
(CH]CCH2OC]O), 185.1 (CH]CHC(O)CH]CH), 194.7 (C]CHC]
O); MS (ESIþ) m/z (%) 495 [MþNa]þ (100), 143 (95), 245 (65), 217
(40); HRMS (ESIþ) m/z found 495.2717. C28H40O6Na requires
495.2718.
Supplementary data
Supplementary data associated with this article can be found in
References and notes
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