NATURAL PRODUCT RESEARCH
5
(C-11), 122.3 (C-12), 143.9 (C-13), 43.9 (C-14), 29.7 (C-15), 22.2 (C-16), 46.6 (C-17), 41.3
(
2
2
C-18), 45.9 (C-19), 30.7 (C-20), 33.4 (C-21), 33.8 (C-22), 28.1 (C-23), 15.3 (C-24), 15.6 (C-
0
ꢁ
5), 18.3 (C-26), 23.0 (C-27), 177.8 (C-28), 33.0 (C-29), 23.6 (C-30), 64.3 (C-1 ), 28.2 (C-
0
ꢁ
0
0
0
ꢁ
), 28.3 (C-3 ), 25.9 (C-4 ), 14.0 (C-5 ). Values may be interchanged.
Hexyl oleanolate (6). Yield 67%. White amorphous solid. EIMS m/z (rel. int. %): 540
þ
1
[
(
M ] (5), 411 (8), 332 (15), 293 (34), 203 (30), 189 (10), 167 (20), 149 (100). H NMR
CDCl3) d: 3.19 (1H, dd, J ¼ 11.0, 4.0 Hz, H-3a), 5.26 (1H, t, J ¼ 4.0 Hz, H-12), 2.85 (1H,
dd, J ¼ 14.0, 4.5 Hz, H-18b), 1.11, 0.97, 0.90, 0.88, 0.87, 0.76, 0.71 (each 3H, s, 7XCH ),
3
0
0
3
.98 (2H, m, H-1 ), 0.88 (3H, t, J ¼ 6.9 Hz, H-6 ).
Heptyl oleanolate (7). Yield 68%. White amorphous solid. EIMS m/z (rel. int. %): 554
8), 537 (5), 410 (15), 393 (10), 346 (31), 333 (12), 203 (100), 189 (33). H NMR (CDCl )
1
(
3
d: 3.19 (1H, dd, J ¼ 9.9, 4.2 Hz, H-3a), 5.25 (1H, t, J ¼ 3.3 Hz, H-12), 2.85 (1H, dd, J ¼ 14.1,
4
1
.5 Hz, H-18b), 1.11, 0.97, 0.90, 0.88, 0.88, 0.76, 0.71 (each 3H, s, 7XCH ), 3.98 (2H, m, H-
3
0
0
13
), 0.87 (3H, t, J ¼ 6.8 Hz, H-7 ). C NMR (CDCl , 75 MHz): d 38.4 (C-1), 27.2 (C-2), 79.0
3
(
(
(
C-3), 38.4 (C-4), 55.2 (C-5), 17.0 (C-6), 33.0 (C-7), 39.3 (C-8), 47.6 (C-9), 38.4 (C-10), 23.4
C-11), 122.6 (C-12), 143.9 (C-13), 43.9 (C-14), 29.7 (C-15), 23.5 (C-16), 46.6 (C-17), 41.3
C-18), 45.9 (C-19), 30.7 (C-20), 33.4 (C-21), 33.8 (C-22), 28.1 (C-23), 15.3 (C-24), 15.6 (C-
0
ꢁ
2
2
5), 18.3 (C-26), 23.0 (C-27), 177.8 (C-28), 33.0 (C-29), 23.6 (C-30), 64.3 (C-1 ), 28.8 (C-
0
0
ꢁ
0
0
0
0
ꢁ
), 26.0 (C-3 ), 28.6 (C-4 ), 31.8 (C-5 ), 25.9 (C-6 ), 14.1(C-7 ). Values may be
interchanged.
Octyl oleanolate (8). Yield 73%. White amorphous solid. EIMS m/z (rel. int. %): 568
þ
1
[
M ] (10), 550 (5), 410 (29), 393 (8), 360 (81), 347 (17), 203 (100), 189 (60), 133 (20). H
NMR (CDCl ) d: 3.19 (1H, dd, J ¼ 10.2, 4.5 Hz, H-3a), 5.26 (1H, t, J ¼ 3.0 Hz, H-12), 2.83
3
(
7
(
(
(
1H, dd, J ¼ 14.1, 4.2 Hz, H-18b), 1.11, 0.96, 0.90, 0.88, 0.88, 0.76, 0.71 (each 3H, s,
0
0
13
XCH ), 3.98 (2H, m, H-1 ), 0.86 (3H, t, J ¼ 7.0 Hz, H-8 ). C NMR (CDCl , 75 MHz): d 38.4
3
3
C-1), 28.1 (C-2), 79.0 (C-3), 38.7 (C-4), 55.2 (C-5), 17.0 (C-6), 33.1 (C-7), 39.3 (C-8), 47.7
C-9), 37.0 (C-10), 23.6 (C-11), 122.3 (C-12), 143.9 (C-13), 41.3 (C-14), 29.2 (C-15), 22.7
C-16), 46.7 (C-17), 41.3 (C-18), 45.6 (C-19), 30.7 (C-20), 33.9 (C-21), 32.8 (C-22), 27.7 (C-
2
3
1
3), 15.3 (C-24), 15.6 (C-25), 18.0 (C-26), 23.4 (C-27), 177.8 (C-28), 32.5 (C-29), 23.4 (C-
0
0
0
ꢁ
0
ꢁ
0
0
0
0), 64.2 (C-1 ), 28.2 (C-2 ), 26.0 (C-3 ), 29.2 (C-4 ), 29.1 (C-5 ), 31.7 (C-6 ), 25.9 (C-7 ),
0
ꢁ
4.1 (C-8 ). Values may be interchanged.
Nonayl oleanolate (9). Yield 77%. White amorphous solid. EIMS m/z (rel. int. %): 582
[
Mþ] (25), 408 (49), 393 (11), 374 (81), 361 (28), 203 (100), 189 (78), 173 14), 133 (23).
1
H NMR (CDCl ) d: 3.19 (1H, dd, J ¼ 10.8, 4.0 Hz, H-3a), 5.26 (1H, t, J ¼ 3.2 Hz, H-12),
3
2
7
3
4
2
2
2
3
.83 (1H, dd, J ¼ 14.0, 4.4 Hz, H-18b), 1.11, 0.97, 0.90, 0.88, 0.88, 0.76, 0.72 (each 3H, s,
0
0
13
XCH ), 3.98 (2H, m, H-1 ), 0.84 (3H, t, J ¼ 6.8 Hz, H-9 ). C NMR (CDCl , 125 MHz): d
3
3
8.2 (C-1), 27.7 (C-2), 78.5 (C-3), 38.8 (C-4), 55.7 (C-5), 17.0 (C-6), 33.4 (C-7), 38.9 (C-8),
7.1 (C-9), 36.5 (C-10), 23.1 (C-11), 121.8 (C-12), 142.9 (C-13), 41.2 (C-14), 28.1 (C-15),
2.6 (C-16), 46.1 (C-17), 40.0 (C-18), 45.4 (C-19), 31.3 (C-20), 33.4 (C-21), 32.6 (C-22),
7.2 (C-23), 14.8 (C-24), 15.0 (C-25), 18.3 (C-26), 22.5 (C-27), 177.8 (C-28), 32.2 (C-29),
0
ꢁ
0
ꢁꢁ
0
ꢁ
0
0
0
2.9 (C-30), 63.8 (C-1 ), 28.8 (C-2 ), 25.6 (C-3 ), 28.7 (C-4 ), 30.2 (C-5 ), 29.0 (C-6 ),
0
ꢁꢁ ꢁ ꢁꢁ
0
0
1.9 (C-7 ), 25.4 (C-8 ), 13.6 (C-9 ). ,
Values may be interchanged.
Decyl oleanolate (10). Yield 75%. White amorphous solid. EIMS m/z (rel. int. %): 596
1
[
Mþ] (8), 578 (5), 410 (15), 388 (34), 203 (100), 188 (26). H NMR (CDCl ) d: 3.20 (1H,
3
dd, J ¼ 9.3, 3.3 Hz, H-3a), 5.26 (1H, t, J ¼ 3.3 Hz, H-12), 2.84 (1H, dd, J ¼ 14.4, 4.5 Hz, H-