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DOI: 10.1055/s-0029-1217815
Total Synthesis of New Lipocarbazoles Isolated from the Actinomycete Tsukamurella pseudospumae Acta 1857 [¹]
Publication History
Publication Date:
17 August 2009 (online)
Abstract
New lipocarbazoles were synthesized by a sequence of three palladium-mediated coupling reactions and an improved protecting group strategy.
Key words
heterocycles - cross-coupling - total synthesis - hydroboration - natural products
Article 50 in the series ‘Biosynthetic Capacities of Actinomycetes’.
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References and Notes
Article 50 in the series ‘Biosynthetic Capacities of Actinomycetes’.
3Schneider, K.; Nachtigall, J.; Hänchen, A.; Nicholson, G.; Goodfellow, M.; Süssmuth, R. D.; Fiedler, H.-P. J. Nat. Prod. 2009, submitted.
23
Spectral Data
for Lipocarbazole A4 (1a)
IR (neat): ν = 3466,
3388, 2920, 2849, 1500, 1466, 1436, 1311, 1233, 1147, 1064, 830,
772, 738 cm-¹. ¹H
NMR (400 MHz, DMSO-d
6): δ = 10.65
(s, 1 H), 8.78 (s, 1 H), 7.87-7.85 (d, J = 8.0
Hz, 1 H), 7.41-7.39 (d, J = 8.0
Hz, 1 H), 7.28-7.24 (t, J = 8.0
Hz, 1 H), 7.26 (s, 1 H), 7.04-7.00 (t, J = 8.0 Hz,
1 H), 2.88-2.84 (t, J = 8.0
Hz, 2 H), 2.22 (s, 3 H), 1.57-1.50 (m, 2 H), 1.45-1.38
(m, 2 H), 1.23 (br s, 13 × 2 H), 0.86-0.82
(t, J = 8.0
Hz, 3 H) ppm. ¹³C NMR (100 MHz, DMSO-d
6): δ = 148.93,
139.97, 133.24, 124.36, 123.95, 122.73, 121.30, 119.64, 119.48,
117.48, 110.75, 101.87, 31.32, 29.36, 29.33, 29.14, 29.12, 29.05,
28.73, 28.12, 22.13, 13.97, 12.17 ppm. MS (EI): m/z (%) = 435
(100), 267 (10), 210 (38), 167 (4), 97 (3), 83 (4), 69 (5), 57 (7).
HRMS (EI): m/z calcd for C30H45NO [M]+:
435.3501; found: 435.3500.
Spectral Data
for Lipocarbazole A3 (1b)
IR (neat): ν = 3471,
3382, 2923, 2853, 1593, 1500, 1461, 1436, 1311, 1231, 1146, 1062,
831, 772, 739 cm-¹. ¹H
NMR (400 MHz, DMSO-d
6): δ = 10.65
(s, 1 H), 8.79 (s, 1 H), 7.87-7.85 (d, J = 8.0
Hz, 1 H), 7.41-7.39 (d, J = 8.0
Hz, 1 H), 7.28-7.24 (t, J = 8.0
Hz, 1 H), 7.26 (s, 1 H), 7.04-7.00 (t, J = 8.0
Hz, 1 H), 5.35-5.27 (2 × 1 H),
2.89-2.85 (t, J = 8.0 Hz,
2 H), 2.22 (s, 3 H), 1.98-1.94 (m, 2 × 2
H), 1.57-1.50 (m, 2 H), 1.46-1.39 (m, 2 H), 1.29-1.21
(m, 9 × 2 H), 0.85-0.81 (t, J = 8.0 Hz,
3 H) ppm. ¹³C NMR (100 MHz, DMSO-d
6): δ = 149.00,
140.04, 133.31, 129.74, 129.71, 124.46, 124.02, 122.80, 121.37,
119.71, 119.57, 117.58, 110.83, 101.96, 31.36, 29.37, 29.22, 29.17,
29.01, 28.90, 28.77, 28.67, 28.19, 26.67, 26.65, 22.17, 14.02, 12.07
ppm. MS (EI): m/z (%) = 433
(94), 210 (100), 196 (6), 180 (12), 167 (11), 97 (3), 83 (4), 69
(5), 57 (8), 55 (9). HRMS (EI): m/z calcd
for C30H43NO [M]+:
433.3345; found: 433.3342.
Spectral Data
for Lipocarbazole A2 (1c)
IR (neat): ν = 3471,
3381, 3009, 2924, 2853, 1593, 1499, 1461, 1436, 1311, 1230, 1146,
1062, 831, 772, 739 cm-¹. ¹H NMR
(400 MHz, DMSO-d
6): δ = 10.65
(s, 1 H), 8.79 (s, 1 H), 7.87-7.85 (d, J = 8.0
Hz, 1 H), 7.41-7.39 (d, J = 8.0 Hz,
1 H), 7.28-7.24 (t, J = 8.0
Hz, 1 H), 7.26 (s, 1 H), 7.04-7.00 (t, J = 8.0
Hz, 1 H), 5.37-5.25 (4 × 1H),
2.89-2.85 (t, J = 8.0
Hz, 2 H), 2.74-2.70 (t, J = 8.0
Hz, 2 H), 2.22 (s, 3 H), 2.00-1.97 (m, 2 × 2
H), 1.57-1.50 (m, 2 H), 1.46-1.39 (m, 2 H), 1.30-1.21
(m, 6 × 2 H), 0.85-0.81 (t, J = 8.0 Hz,
3 H). ¹³C NMR (100 MHz, DMSO-d
6): δ = 148.93,
139.96, 133.24, 129.72, 127.77, 127.73, 124.37, 123.94, 122.72, 121.30,
119.63, 119.49, 117.50, 110.75, 101.88, 30.89, 29.33, 29.30, 29.07,
28.95, 28.73, 28.10, 26.63, 26.61, 25.23, 21.97, 13.91, 11.99. MS
(EI): m/z (%) = 431
(58), 210 (100), 196 (9), 180 (15), 167 (17), 91 (5). HRMS (EI): m/z calcd for C30H45NO [M]+:
431.3188; found: 431.3191.