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1.6.5.1.7 Formal Synthesis of (+)-Nakadomarin A

DOI: 10.1055/sos-SD-219-00294

Shi, L.; Yang, Z.Science of Synthesis: Applications of Domino Transformations in Organic Synthesis, (20151611.

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,[‌92‌‌95‌] and several synthetic studies.[‌96‌‌103‌]

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References


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