The Asymmetric Total Synthesis of Nakadomarin A, a Marine Manzamine Alkaloid
نویسندگان
چکیده
منابع مشابه
Efficient total synthesis of marine alkaloid (-)-nakadomarin A.
In 1997, Kobayashi and co-workers disclosed the isolation of ( )-nakadomarin A (1, Scheme 1) from an Okinawan marine sponge Amphimedon sp. Its unique 8/5/5/5/15/6 hexacyclic full-ring structure containing four stereogenic centers and an imbedded furan was shown with extensive NMR spectroscopic analyses including NOE and proton coupling data. The biological properties of 1 range from prominent c...
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The total synthesis of (+)-nakadomarin A is described. A three-component cycloaddition of a hydroxylamine, aldehyde, and cyclopropane to form a highly functionalized tetrahydro-1,2-oxazine serves as the foundation for this synthesis. The resulting oxazine is formed as a single diastereomer with the absolute configuration being dictated by the chirality of the cyclopropane. Other key steps inclu...
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In the present paper, we report an efficient total synthesis of a marine alkaloid, rigidin E. The key tetrasubstituted 2-amino-3-carboxamidepyrrole intermediate was synthesized by cascade Michael addition/intramolecular cyclization between N-(2-(4-(benzyloxy)phenyl)-2-oxoethyl)methanesulfonamide and 3-(4-(benzyloxy)phenyl)-2-cyano-N-methylacrylamide. Subsequent carbonylation with triphosgene ca...
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A new monoterpenoid indole alkaloid, kopsiyunnanine K, was isolated from Kopsia arborea. Its intriguing rearranged structure and absolute configuration, which were inferred from spectral data and a possible biosynthetic pathway, were determined on the basis of a 13-step asymmetric total synthesis.
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Concise and highly stereocontrolled total syntheses of racemic and enantiopure frog alkaloid 205B (1) were accomplished in 11 steps from 4-methoxypyridines 6 and 7 in overall yields of 8 and 8%, respectively. The assembly of the core of the natural product relies on a stereoselective Tsuji-Trost allylic amination reaction and a ring-closing metathesis. The synthesis features the use of an N-acy...
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ژورنال
عنوان ژورنال: Journal of Synthetic Organic Chemistry, Japan
سال: 2005
ISSN: 0037-9980,1883-6526
DOI: 10.5059/yukigoseikyokaishi.63.200