jo061813u_si_008.cif (19.53 kB)
Total Synthesis of the Cytostatic Marine Natural Product Dibromophakellstatin via Three-Component Imidazolidinone Anellation
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posted on 2006-12-08, 00:00 authored by Michael Zöllinger, Peter Mayer, Thomas LindelThe tetracyclic pyrrole−imidazole alkaloid dibromophakellstatin from the marine sponge Phakellia
mauritiana has been synthesized within seven steps from pyrrole in an 18% overall yield. The key step
is a three-component assembly of a tricyclic enamide, a nitrene, and a carbamoyl building block, affording
the imidazolidinone ring of dibromophakellstatin in one step. Notably, it is possible to employ the reagent
EtO2CNHOTs in a double function as a source of the electrophilic nitrene and of a dipolar carbamoyl
component. Use of debrominated precursor dipyrrolopyrazinones leads to much higher anellation yields
and allowed us to develop a second generation synthesis. The cytostatic activity of dibromophakellstatin
is confirmed.
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dipolar carbamoyl componentCytostatic Marine Natural Product Dibromophakellstatinpyrrolemarine sponge Phakellia mauritianaelectrophilic nitrenegeneration synthesisanellation yieldsreagent EtO 2CNHOTsimidazolidinone ringcarbamoyl building blockdibromophakellstatincytostatic activitydebrominated precursor dipyrrolopyrazinonesTotal Synthesistricyclic enamide
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