MERKHATULY et al.
758
(1Н, Н13, J 3.5 Hz), 5,92 d (1Н, H15, J 1 Hz), 6.26 d
Scheme 2.
(1Н, Н13, J 3.5 Hz). Mass spectrum, m/z (Irel, %): 248
(44.7) [М]+. Found, %: С 72.33; Н 7.81. С15Н20О3.
Calculated, %: С 72.58; Н 8.06.
OH
OH
H
O
H
H
O
H
IR spectra were recorded on a spectrophotometer
HO
O
1
H
H
Avatar-360 from pellets with KBr. Н NMR spectra
were registered on a spectrometer Bruker Avance-400
(operating frequency 400.13 МHz), solvent СDCl3,
internal reference TMS. Mass spectra were obtained on
an instrument Agilent 7890А. Specific rotation was
measured on a polarimeter Perkin-Elmer 141. Melting
points were determined on a small heating block
Boёtius. TLC was carried out on Silufol UV-254
plates.
O
O
IV
V
[α]D18 +96о (с 0.02, CHCl3). IR spectrum, ν, cm–1: 1760
1
(С=О), 1700 (С=О), 1640 (С=С). Н NMR spectrum,
δ, ppm: 1.43 s (3Н, СН3-С10), 1.68 br.s (3Н, СН3-С4),
4.12 q (1Н, Н6, J 10, 8.5 Hz), 5.52 d (1Н, Н13, J 3.5 Hz),
6.26 d (1Н, Н13, J 3.5 Hz). Mass spectrum, m/z (Irel,
%): 248 (32.4) [М]+. Found, %: С 72.38; Н 7.87.
С15Н20О3. Calculated, %: С 72.58; Н 8.06.
REFERENCES
3-Hydroxyeudesma-4(15),11(13)-dien-6,12-olide,
or (3aS,5aS,9aR,9bS)-8-hydroxy-5a-methyl-3,9-
dimethylidenedecahydronaphtho[1,2-b]furan-
2(3H)-one (III). Yield 0. 074 g (30%). Rf 0.37
(hexane–ethyl acetate, 1 : 4). Colorless crystals, mp
175–177°С. [α]D18 +106о (с 0.02, CHCl3). IR spectrum,
1. Merkhatuly, N., Zhokizhanova, S.K., Balmagambe-
tova, L.T., and Adekenov, S.M., Russ. J. Gen. Chem.,
2006, vol. 76, p. 1347.
2. Merkhatuly, N., Vestn. Karagand. Gos. Univer., Ser.
Khim., 2008, no 2, p. 46
3. Irwin, M.A. and Geissman, T.A., Phytochem., 1973,
vol. 12, p. 871.
4. Geissman, T.A., Griffin, T.S., and Irwin, M.A.,
Phytochem., 1969, vol. 8, p. 871.
1
ν, cm–1: 1760 (С=О), 1650, 1640 (С=С). Н NMR
spectrum, δ, ppm: 1.43 s (3Н, СН3С10), 4.12 q (1Н,
Н6, J 10, 8.5 Hz), 5,26 d (1Н, H15, J 1 Hz), 5.52 d
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 5 2014