Journal of Natural Products
Article
4, NCH3), 1.89 (2H, m, OCH2CH2CH2CH2CH3), 1.50−1.37 (4H, m,
dd, J = 16.1, 3.0 Hz, H-7b), 2.59−2.47 (5H, m, H-5, 4, NCH3), 1.89−
1.85 [1H, m, CH(CH3CH2)CH3], 1.70−1.65 [1H, m, CH(CH3CH2)-
CH3], 1.39−1.35 [3H, m, CH(CH3CH2)CH3], 1.04−0.99 [3H, m,
CH(CH3CH2)CH3]; 13C NMR (125 MHz, CDCl3) δ 151.9 (C-2),
148.8 (C-10), 146.8 (C-9), 144.3 (C-1), 129.2 (C-7a), 128.8 (C-1a),
127.3 (C-3a), 126.9 (C-1b), 124.6 (C-11a), 114.7 (C-8), 112.3 (C-
11), 110.3 (C-3), 76.5 [CH(CH3CH2)CH3], 62.6 (C-6a), 60.1 (C-1-
OCH3), 56.0 (C-10-OCH3), 55.7 (C-2-OCH3), 53.3 (C-5), 44.1
(NCH3), 34.5 (C-7), 29.3 (C-4), 29.2 [CH(CH3CH2)CH3], 19.4
[CH(CH3CH2)CH3], 10.0 [CH(CH3CH2)CH3]; HRESIMS m/z
398.2328 [M + H]+ (calcd for C24H31NO4, 398.2331).
OCH2 CH2 CH2 CH2 CH3 ), 0.94 (3H, t,
J = 7.2 Hz,
OCH2CH2CH2CH2CH3); 13C NMR (125 MHz, CDCl3) δ 151.9
(C-2), 147.8 (C-10), 147.6 (C-9), 144.2 (C-1), 129.3 (C-7a), 128.9
(C-1a), 127.3 (C-3a), 126.9 (C-1b), 124.3 (C-11a), 112.2 (C-8), 111.9
(C-11), 110.3 (C-3), 68.8 (OCH2CH2CH2CH2CH3), 62.6 (C-6a),
60.1 (C-1-OCH3), 56.0 (C-10-OCH3), 55.7 (C-2-OCH3), 53.3 (C-5),
44.1 (NCH3), 34.6 (C-7), 29.3 (C-4), 28.9 (OCH2CH2CH2CH2CH3),
28.1 (OCH2CH2CH2CH2CH3), 22.5 (OCH2CH2CH2CH2CH3), 14.0
(OCH2CH2CH2CH2CH3); HRESIMS m/z 412.2456 [M + H]+ (calcd
for C25H33NO4, 412.2488).
(S)-9-(Hexyloxy)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetra-
hydro-4H-dibenzo[de,g]quinoline, 10d. Yield: 83% (72 mg), light
brown gum; Rf = 0.54 on silica gel TLC plate in 5:95 MeOH−CH2Cl2;
1H NMR (500 MHz, CDCl3) δ 8.08 (1H, s, H-11), 6.77 (1H, s, H-8),
(S)-1,2,10-Trimethoxy-6-methyl-9-(pentan-2-yloxy)-5,6,6a,7-
tetrahydro-4H-dibenzo[de,g]quinoline, 10h. Yield: 86% (72 mg),
light brown gum; Rf = 0.56 on a silica gel TLC plate in 5:95 MeOH−
CH2Cl2; 1H NMR (500 MHz, CDCl3) δ 8.08 (1H, s, H-11), 6.78 (1H,
s, H-8), 6.58 (1H, s, H-3), 4.43−4.39 [1H, m, OCH(CH2CH2CH3)-
CH3], 3.88 (3H, s, OCH3-2), 3.86 (3H, s, OCH3-10), 3.66 (3H, s,
OCH3-1), 3.18−3.11 (1H, m, H-4), 3.05−2.96 (3H, m, H-5, 6a, 7a),
2.67 (1H, dd, J = 16.1, 2.8 Hz, H-7b), 2.59−2.48 (5H, m, H-5, 4,
NCH3), 1.89−1.81 [1H, m, OCH(CH2CH2CH3)CH3], 1.65−1.35
[6H, m, OCH(CH2CH2CH3)CH3], 0.98−0.94 [3H, m, OCH-
(CH2CH2CH3)CH3]; 13C NMR (125 MHz, CDCl3) δ 151.9 (C-2),
148.8 (C-10), 146.8 (C-9), 144.3 (C-1), 129.2 (C-7a), 128.8 (C-1a),
127.3 (C-3a), 126.9 (C-1b), 124.6 (C-11a), 114.7 (C-8), 112.3 (C-
11), 110.3 (C-3), 75.0 [OCH(CH2CH2CH3)CH3], 62.6 (C-6a), 60.1
(C-1-OCH3), 56.0 (C-10-OCH3), 55.7 (C-2-OCH3), 53.3 (C-5), 44.0
(NCH3), 38.8 [OCH(CH2CH2CH3)CH3], 34.5 (C-7), 29.3 (C-4),
19.9 (OCH(CH2CH2CH3)CH3), 18.9 [OCH(CH2CH2CH3)CH3],
14.1 [OCH(CH2CH2CH3)CH3]; HRESIMS m/z 412.2485 [M + H]+
(calcd for C25H33NO4, 412.2488).
(S)-9-(Hexan-2-yloxy)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-
tetrahydro-4H-dibenzo[de,g]quinoline, 10i. Yield: 74 mg, 85%
(74 mg), light brown gum; Rf = 0.56 on a silica gel TLC plate in 5:95
MeOH−CH2Cl2; 1H NMR (500 MHz, CDCl3) δ 8.08 (1H, s, H-11),
6.77 (1H, s, H-8), 6.58 (1H, s, H-3), 4.42−4.38 [1H, m,
OCH(CH2CH2CH2CH3)CH3], 3.88 (3H, s, OCH3-2), 3.86 (3H, s,
OCH3-10), 3.66 (3H, s, OCH3-1), 3.18−3.11 (1H, m, H-4), 3.05−
2.96 (3H, m, H-5, 6a, 7a), 2.67 (1H, dd, J = 16.1, 3.0 Hz, H-7b), 2.59−
2.47 (5H, m, H-5, 4, NCH3), 1.90−1.82 (1H, m, OCH-
(CH2 CH2 CH2 CH3 )CH3 ), 1.67−1.59 [1H, m, OCH-
(CH2 CH2 CH2 CH3 )CH3 ], 1.53−1.49 [1H, m, OCH-
(CH2 CH2 CH2 CH3 )CH3 ], 1.48−1.35 [6H, m, OCH-
( C H 2 C H 2 C H 2 C H 3 ) C H 3 ] , 0 . 9 4 − 0 . 9 0 [ 3 H , m ,
OCH(CH2CH2CH2CH3)CH3]; 13C NMR (125 MHz, CDCl3) δ
151.9 (C-2), 148.8 (C-10), 146.8 (C-9), 144.3 (C-1), 129.2 (C-7a),
128.8 (C-1a), 127.3 (C-3a), 127.0 (C-1b), 124.6 (C-11a), 114.7 (C-8),
112.3 (C-11), 110.3-(C-3), 75.3 [OCH(CH2CH2CH2CH3)CH3], 62.6
(C-6a), 60.1 (C-1-OCH3), 56.0 (C-10-OCH3), 55.7 (C-2-OCH3), 53.3
(C-5), 44.1 (NCH3), 36.3 [OCH(CH2CH2CH2CH3)CH3], 34.6 (C-
7), 29.3 (C-4), 27.9 (OCH(CH2CH2CH2CH3)CH3), 22.7 [OCH-
(CH2CH2CH2CH3)CH3], 20.0 [OCH(CH2CH2CH2CH3)CH3], 14.1
[OCH(CH2CH2CH2CH3)CH3]; HRESIMS m/z 426.2631 [M + H]+
(calcd for C26H35NO4, 426.2644).
6.58 (1H, s, H-3), 4.10−4.02 (2H, m, OCH2CH2CH2CH2CH2CH3),
3.88 (6H, s, OCH3-2, OCH3-10), 3.65 (3H, s, OCH3-1), 3.18−3.11
(1H, m, H-4), 3.05−2.98 (3H, m, H-5, 6a, 7a), 2.67 (1H, dd, J = 16.1,
3.1 Hz, H-7b), 2.60−2.48 (5H, m, H-5, 4, NCH3), 1.88 (2H, m,
OCH2CH2CH2CH2CH2CH3), 1.51−1.45 (2H, m, OCH2CH2CH2-
CH2CH2CH3), 1.39−1.33 (4H, m, OCH2CH2CH2CH2CH2CH3),
0.92−0.89 (3H, m, 3H, OCH2CH2CH2CH2CH2CH3); 13C NMR
(125 MHz, CDCl3) δ 151.9 (C-2), 147.8 (C-10), 147.6 (C-9), 144.2
(C-1), 129.3 (C-7a), 128.8 (C-1a), 127.2 (C-3a), 126.9 (C-1b), 124.3
(C-11a), 112.2 (C-8), 111.9 (C-11), 110.3 (C-3), 68.9
(OCH2CH2CH2CH2CH2CH3), 62.6 (C-6a), 60.1 (C-1-OCH3), 56.0
(C-10-OCH3), 55.7 (C-2-OCH3), 53.3 (C-5), 44.0 (NCH3), 34.5 (C-
7), 31.6 (OCH2CH2CH2CH2CH2CH3), 29.3 (C-4), 29.2
(OCH2CH2CH2CH2CH2CH3), 25.7 (OCH2CH2CH2CH2CH2CH3),
22.6 (OCH2CH2CH2CH2CH2CH3), 14.0 (OCH2CH2CH2-
CH2CH2CH3); HRESIMS m/z 426.2644 [M + H]+ (calcd for
C26H35NO4, 426.2644).
(S)-9-(2-Fluoroethoxy)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-
tetrahydro-4H-dibenzo[de,g]quinoline, 10e. Yield: 80% (63 mg),
light brown gum; Rf = 0.57 on a silica gel TLC plate in 5:95 MeOH−
CH2Cl2; 1H NMR (500 MHz, CDCl3) δ 8.10 (1H, s, H-11), 6.82 (1H,
s, H-8), 6.60 (1H, s, H-3), 4.85 (2H, dt, J = 47.5, 4.5 Hz,
OCH2CH2F), 4.39−4.27 (2H, m, OCH2CH2F), 3.89 (3H, s, OCH3-
2), 3.88 (3H, s, OCH3-10), 3.65 (3H, s, OCH3-1), 3.18−3.11 (1H, m,
H-4), 3.05−2.97 (3H, m, H-5, 6a, 7a), 2.67 (1H, dd, J = 16.2, 3.2 Hz,
H-7b), 2.59−2.47 (5H, m, H-5, 4, NCH3); 13C NMR (125 MHz,
CDCl3): δ 151.9 (C-2), 148.1 (C-10), 146.8 (C-9), 144.3 (C-1), 129.3
(C-7a), 128.9 (C-1a), 127.3 (C-3a), 126.7 (C-1b), 125.6 (C-11a),
113.6 (C-8), 112.3 (C-11), 110.5 (C-3), 82.6 (OCH2CH2F), 68.4
(OCH2CH2F), 62.5 (C-6a), 60.1 (C-1-OCH3), 56.0 (C-10-OCH3),
55.7 (C-2-OCH3), 53.3 (C-5), 44.0 (NCH3), 34.4 (C-7), 29.3 (C-4);
HRESIMS m/z 388.2548 [M + H]+ (calcd for C22H26FNO4,
388.1924).
(S)-9-Isopropoxy-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetra-
hydro-4H-dibenzo[de,g]quinoline, 10f. Yield: 83% (65 mg), light
brown gum; Rf = 0.55 on silica gel TLC plate in 5:95 MeOH−CH2Cl2;
1H NMR (500 MHz, CDCl3) δ 8.08 (1H, s, H-11), 6.78 (1H, s, H-8),
6.58 (1H, s, H-3), 4.60 [1H, sept., J = 6.1 Hz, OCH(CH3)2], 3.88 (3H,
s, OCH3-2), 3.87 (3H, s, OCH3-10), 3.65 (3H, s, OCH3-1), 3.18−3.12
(1H, m, H-4), 3.05−2.96 (3H, m, H-5, 6a, 7a), 2.67 (1H, dd, J = 16.2,
3.2 Hz, H-7b), 2.59−2.48 (5H, m, H-5, 4, NCH3), 1.43−1.40 [6H, d, J
= 6.1 Hz, OCH(CH3)2]; 13C NMR (125 MHz, CDCl3) δ 151.9 (C-2),
148.6 (C-10), 146.4 (C-9), 144.2 (C-1), 129.2 (C-7a), 128.8 (C-1a),
127.3 (C-3a), 126.9 (C-1b), 124.6 (C-11a), 114.5 (C-8), 112.1 (C-
11), 110.3 (C-3), 71.1 [OCH(CH3)2], 62.5 (C-6a), 60.1 (C-1-OCH3),
55.9 (C-10-OCH3), 55.7 (C-2-OCH3), 53.3 (C-5), 44.0 (NCH3), 34.5
(C-7), 29.3 (C-4), 22.3 [OCH(CH3)2], 22.3 [OCH(CH3)2];
HRESIMS m/z 384.2163 [M + H]+ (calcd for C23H29NO4, 384.2175).
(S)-9-(sec-Butoxy)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tet-
rahydro-4H-dibenzo[de,g]quinoline, 10g. Yield: 75% (61 mg),
light brown gum; Rf = 0.55 on silica gel TLC plate in 5:95 MeOH−
CH2Cl2; 1H NMR (500 MHz, CDCl3) δ 8.08 (1H, s, H-11), 6.77 (1H,
s, H-8), 6.58 (1H, s, H-3), 4.37−4.31 [1H, m, CH(CH3CH2)CH3],
3.88 (3H, s, OCH3-2), 3.87 (3H, s, OCH3-10), 3.66 (3H, s, OCH3-1),
3.15−3.11 (1H, m, H-4), 3.05−2.96 (3H, m, H-5, 6a, 7a), 2.67 (1H,
(S)-9-(Cyclopropylmethoxy)-1,2,10-trimethoxy-6-methyl-
5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline, 10j. Yield: 84%
(68 mg), light brown gum; Rf = 0.55 on a silica gel TLC plate in 5:95
MeOH−CH2Cl2; 1H NMR (500 MHz, CDCl3) δ 8.09 (1H, s, H-11),
6.77 (1H, s, H-8), 6.58 (1H, s, H-3), 3.90−3.88 [8H, m,
OCH2CH(CH2CH2)], OCH3-2, OCH3-10), 3.65 (3H, s, OCH3-1),
3.18−3.11 (1H, m, H-4), 3.05−2.97 (3H, m, H-5, 6a, 7a), 2.67 (1H,
dd, J = 16.2, 2.8 Hz, H-7b), 2.59−2.48 (5H, m, H-5, 4, NCH3), 1.42−
1.36 [1H, m, OCH2CH(CH2CH2)], 0.68−0.64 [2H, m, OCH2CH-
(CH2CH2)], 0.39−0.36 [2H, m, OCH2CH(CH2CH2)]; 13C NMR
(125 MHz, CDCl3) δ 151.9 (C-2), 147.8 (C-10), 147.5 (C-9), 144.2
(C-1), 129.2 (C-7a), 128.9 (C-1a), 127.2 (C-3a), 126.9 (C-1b), 124.5
(C-11a), 112.5 (C-8), 111.9 (C-11), 110.3 (C-3), 73.8 [OCH2CH-
(CH2CH2)], 62.6 (C-6a), 60.1 (C-1-OCH3), 56.0 (C-10-OCH3), 55.7
(C-2-OCH3), 53.3 (C-5), 44.0 (NCH3), 34.5 (C-7), 29.3 (C-4), 10.3
[OCH2CH(CH2CH2)], 3.5 [OCH2CH(CH2CH2)], 3.5 [OCH2CH-
F
J. Nat. Prod. XXXX, XXX, XXX−XXX