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Synfacts 2010(3): 0272-0272  
DOI: 10.1055/s-0029-1219255
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Nakadomarin A

Contributor(s): Steven V. Ley, Kimberley A. Roper
P. Jakubec, D. M. Cockfield, D. J. Dixon*
University of Oxford and the University of Manchester, UK
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Publikationsverlauf

Publikationsdatum:
18. Februar 2010 (online)

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Significance

(-)-Nakadomarin A is marine alkaloid with an unusual 8/5/5/5/15/6 ring system. This total synthesis significantly reduces the longest linear sequence from 36 in the original synthesis by Nishida to 12 steps. This successful route relies on a stereoselective Michael addition, nitro-Mannich-lactamization cascade and finally a Z-selective ring-closing metathesis.