Journal of Asian Natural Products Research
151
J ¼ 10.6 Hz, H-C-28) and dH 3.68 (d, 1H,
J ¼ 10.6 Hz, H-C-28), 9.56 (s, 1H, alde-
hyde hydrogen at C-30). Two acetyl
methyls appeared at dH 2.07 (s, 3H) and at
2.03 (s, 3H). C-3 hydrogen appeared as a
broad multiplet centeredat dH 4.44 (m, 1H).
Elemental analysis: found: C, 75.42%, H,
9.56%; cacld for C34H52O5: C, 75.51%, H,
9.69%.
ified by column chromatography over
silica gel (60–120 mesh).
Compound 8 was obtained (72%) as a
white solid, mp 260–2628C, IR nmax: 3461
(ZOH), 1732 (ZOCOCH3), 1691 (.
CvCZCHO), 1459, 1369 (gem dimethyl),
1244, 1028, 978, 936, 890 (vCH2) cm21
.
1H NMR dH 0.75 (s, 3H), 0.80 (s, 3H), 0.89
(s, 3H), 0.92 (s, 3H), 0.95 (s, 3H), 2.1 (s, 3H,
acetate methyl), 3.18 (m, 1H, proton at C-
3), 3.38 (d, 1H, J ¼ 10.6 Hz, H-C-28), 3.83
(d, 1H, J ¼ 10.6 Hz, H-C-28), 5.94 (s, 1H,
H-C-29), 6.32 (s, 1H, H-C-29), 9.56 (s, 1H,
aldehyde hydrogen at C-30). Elemental
analysis: found: C, 77.02%, H, 10.12%;
calcd for C32H50O4: C, 77.06%, H, 10.10%.
3.6 Lup-20(29)-en-3b,28-diol-30-al (7)
Compound 6 (900 mg, 1.66 mmol) was
refluxed with 10% (w/v) alcoholic KOH
solution for 4 h. After completion of the
reaction, it was poured into 100 ml ice-
cold water. After usual work up with
diethyl ether, the ether layer was washed
several times with water, dried over
anhydrous sodium sulfate, and the recov-
ered material was purified by column
chromatography over silica gel (60–120
mesh).
3.8 28-Acetoxy-3-oxolup-20(29)-en-30-
al (9)
Compound 8 (150 mg, 0.30 mmol) was
dissolved in dry pyridine (30 ml). Two
hundred and thirty milligrams (2.91 mmol)
of dry CrO3 were added in small lots and
the reaction mixture was kept overnight. It
was then poured into ice-cold water and
the resultant yellowish solid was extracted
with ether, washed with 6 N HCl and again
with water till neutral, and dried over
anhydrous magnesium sulfate to get a
gummy residue. Purification of the gum
over a column of silica gel (60–120 mesh)
yielded compound 9.
Compound 7 was obtained (756 mg,
84%) as a white solid, mp 274–2768C,
IR nmax: 3393 (ZOH), 1688 (.CvCZ
CHO), 1453, 1375 (gem dimethyl), 1029,
942, 890 (vCH2) cm21. 1H NMR: dH 0.75
(s, 3H), 0.81 (s, 3H), 0.95 (s, 3H), 1.00 (s,
3H), 1.38 (s, 3H), 2.62 (m, 1H, hydrogen at
C-3), 3.15 (m, 1H, proton of-OH at C-3),
3.38 (d, 1H, J ¼ 10.6 Hz, H-C-28), 3.83
(d, 1H, J ¼ 10.6 Hz, H-C-28), 5.94 (s, 1H,
H-C-29), 6.32 (s, 1H, H-C-29), 9.56 (s, 1H,
aldehyde hydrogen at C-30). Elemental
analysis: found: C, 78.66%, H, 10.52%;
calcd for C30H48O3: C, 78.90%, H, 10.59%.
Compound 9 was obtained (84 mg,
56%) as a white solid, mp 276–2788C.
IR nmax: 1730 (.CvO), 1706, 1697
(.CvCZCHO), 1461, 1380 (gem
dimethyl), 1244, 1163, 987, 890 (vCH2)
cm21. Elemental analysis: found: C,
77.28%, H, 9.62%; calcd for C32H48O4:
3.7 3b-Hydroxy-28-acetoxy-lup-
20(29)-en-30-al (8)
1
A solution of 7 (350 mg, 0.76 mmol) in
CHCl3 (10 ml) and pyridine (15 ml) was
treated with Ac2O (10 ml, 0.098 mmol) at
very low temperature (0–58C) for 12 h.
The solution was diluted with CHCl3
(20 ml), and then the organic layer was
washed with saturated aq. NaCl
(10 ml £ 3), dried, concentrated, and pur-
C, 77.38%, H, 9.74%. H NMR dH 0.75
(s, 3H), 0.80 (s, 3H), 0.89 (s, 3H), 0.92
(s, 3H), 0.95 (s, 3H), 2.17 (s, 3H, acetate
methyl at C-28) 3.38 (d, 1H, J ¼ 10.6 Hz,
H-C-28), 3.83 (d, 1H, J ¼ 10.6 Hz,
H-C-28), 5.92 (s, 1H, H-C-29), 6.23
(s, 1H, H-C-29), 9.56 (s, 1H, aldehyde
hydrogen at C-30).