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Please login to access the full content or check if you have access via1.6.5.1.7 Formal Synthesis of (+)-Nakadomarin A
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Shi, L.; Yang, Z., Science of Synthesis: Applications of Domino Transformations in Organic Synthesis, (2015) 1, 611.
Nakadomarin A (52) is a representative manzamine-related alkaloid that was isolated from the Okinawan marine sponge Amphimedon sp. (SS-264) by Kobayashi.[90,91] Nakadomarin A (52) exhibits cytotoxicity against murine lymphoma L1210 cells (IC50 1.3 µg/mL), inhibitory activity against cyclin-dependent kinase 4 (IC50 9.9 µg/mL), and antimicrobial activity against a fungus (Trichophyton mentagrophytes, MIC 23 µg/mL) and a Gram-positive bacterium (Corynebacterium xerosis, MIC 11 µg/mL). This marine natural product has a unique fused hexacyclic framework consisting of a series of 6/5/5/5/8/15 rings. Intensive efforts have been directed toward its synthesis, leading thus far to four total syntheses,[92–95] and several synthetic studies.[96–103]
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References
[90] | Meeeeeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
[91] | Meeeeeeee, M.; Meeee, M.; Meeeeeeee, M., Meee Meee. Meee., (8888) 88, 8888. |
[92] | Meeeee, M.; Meeeeeee, M.; Meeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[93] | Mee, M.; Meeeeeee, M.; Meeeeee, M., Meeee. Meee. Mee. Me., (8888) 88, 8888. |
[94] | Meeee, M. M.; Meee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[95] | Meeeeee, M.; Meeeeeeee, M. M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |
[96] | Müeeeeee, M.; Meee, M.; Meeee, M.; Meeeee, M., M. Me. Meee. Mee., (8888) 888, 88888. |
[97] | Müeeeeee, M.; Meee, M.; Meeeeee, M.; Meeeee, M.; Meeee, M.; Meeee, M.; Meeeee, M., Meee.–Mee. M., (8888) 8, 8888. |
[98] | Meeeee, M.; Meeeeee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[99] | Meeeee, M.; Meeeeeee, M. M.; Meeee, M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 888. |
[100] | Meeeeee, M. M.; Meeeeeee, M. M., Mee. Meee., (8888) 8, 8888. |
[101] | Meeee, M. M.; Meeeeeee, M. M.; Meee, M. M., Mee. Meee., (8888) 8, 888. |
[102] | Meeeee, M. M.; Meee, M. M., Mee. Meee., (8888) 8, 8888. |
[103] | Meee, M.; Meee, M.; Meee, M.; Me, M.; Meee, M., Mee. Meee., (8888) 88, 8888. |
[104] | Meeeeee, M.; Meeeeeeee, M.; Meeeeeeee, M.; Meeee, M., Mee. Meee., (8888) 88, 8888. |
[105] | Meeeee, M. M.; Meeeeeeee, M. M.; Meeeee, M. M., Meeee. Meee. Mee. Me., (8888) 88, 8888. |
[106] | Meeeee, M. M.; Meeeeeeee, M. M.; Meeeeeee, M. M., Meeee. Meee. Mee. Me., (8888) 88, 8888. |