VOSTRIKOV et al.
142
compounds V and VI, 90 mg, was subjected first to
acid and then to alkaline hydrolysis (Scheme 2) to
isolate 50 mg of PGF1α. Colorless crystals, mp 100–
102°C, [α]D20 = +20.5° (c = 0.5, THF); published data
[14]: [α]D20 = +24° (c = 0.87, THF), mp 101.5–102.5°C
(from CHCl3–MeOH). IR spectrum, ν, cm–1: 3282,
13C NMR spectra were recorded on a Bruker AM-300
spectrometer at 300.13 and 75.47 MHz, respectively,
using the residual proton and carbon signals of the
solvent as reference. The optical rotations were meas-
ured on a Perkin Elmer 241 MS instrument. Thin-layer
chromatography was performed on Sorbfil plates.
1
1697, 1456. H NMR spectrum, δ, ppm: 0.91 t (3H,
REFERENCES
CH3, J = 6.0 Hz), 1.32 m (4H), 1.45 m (4H), 1.6 m
(12H), 2.19–2.23 m (1H), 2.80 t (2H, 2-H, J = 6.0 Hz),
2.36–2.40 m (1H), 3.36 m (1H, 12-H), 3.60 m (1H),
4.00 m (1H), 4.10 m (1H, 9-H, 11-H, 15-H), 5.40–
5.50 m (2H, 13-H, 14-H). 13C NMR spectrum, δC,
ppm: 14.43 (CH3), 23.79 (C19), 26.03 (C3), 26.42 (C17),
28.32 (C6), 28.78 (C7), 30.16 (C4), 30.76 (C5), 32.96
(C18), 34.79 (C2), 38.36 (C16), 44.28 (C10), 50.17 (C8),
56.29 (C12), 72.16 (C15), 74.05 (C9), 77.85 (C11),
134.58 (C13), 136.36 (C14), 175.99 (CO2).
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[α]D20 = –58.2° (c = 0.5, THF). H NMR spectrum, δ,
1
ppm: 0.95 t (3H, CH3, J = 6.5 Hz), 1.20–1.40 m (12H),
1.45–1.65 m (6H), 2.30 t (2H, 2-H, J = 7.0 Hz), 4.00–
4.15 m (2H), 5.55 d.d (1H, 13-H, J = 15.5, 8.4 Hz),
13
5.65 d.d (1H, 14-H, J = 15.5, 7.5 Hz). C NMR spec-
trum, δC, ppm: 13.96 (CH3), 22.63 (C19), 24.39 (C3),
24.52 (C17), 26.79 (C6), 27.48 (C7), 28.56 (C4), 29.13
(C5), 31.5 (C18), 37.1 (C16), 45.95 (C10), 54.38 (C8),
54.58 (C12), 71.94 (C11), 72.90 (C15), 136.64 (C13),
136.82 (C14), 178.62 (CO2), 215.5 (CO).
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The IR spectra were recorded on a Shimadzu IR
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