ArticleMarine drugs2012
Total synthesis of a marine alkaloid--rigidin E.
Article in Marine drugs, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Quantum Chemical Studies on the Prototropic and Acid/Base Equilibria for 2-Aminopyrrole in Vacuo-Role of CH Tautomers in the Design of Strong Brønsted Imino N-Bases.Molecules (Basel, Switzerland) · 2025Article
- Improved Rigidin-Inspired Antiproliferative Agents with Modifications on the 7-Deazahypoxanthine C7/C8 Ring Systems.Journal of medicinal chemistry · 2024Article
- Marine Pyrrole Alkaloids.Marine drugs · 2021Review
- Total Synthesis of Mycalisine B.Marine drugs · 2019Article
- Anticancer properties of lamellarins.Marine drugs · 2015Review
- Tractable synthesis of multipurpose screening compounds with under-represented molecular features for an open access screening platform.Molecular diversity · 2014Article
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Authors and funding
5 authors.
Funding
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Abstract
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 catalyzed by I(2) and deprotection of benzyl groups afforded rigidin E in 21% overall yield. This strategy has the merits of metal-free reactions, low cost, mild reaction protocols, and easy access to diversity-oriented derivatives for potential structure-activity relationship investigation.
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