Synthesis of the unique angular tricyclic chromone structure proposed for aspergillitine, and its relationship with alkaloid TMC-120B |
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Authors: | Simonetti Sebastián O Larghi Enrique L Bracca Andrea B J Kaufman Teodoro S |
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Institution: | Institute of Chemistry of Rosario (IQUIR, CONICET-UNR) and School of Biochemical and Pharmaceutical Sciences, National University of Rosario, Suipacha 531, S2002LRK Rosario, Argentina. |
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Abstract: | The synthesis of the tricyclic angular chromone structure originally assigned to aspergillitine is reported. The synthesis was achieved in 11 steps and 15% overall yield from 2,4-dihydroxypropiophenone, through the intermediacy of 2,3-dimethyl-7-hydroxychromen-4-one. Construction of the nitrogen-bearing heterocyclic ring entailed a Stille cross-coupling reaction with n-Bu(3)SnCH(2)CH=CH(2), followed by double bond isomerization, oximation of the chromone carbonyl, and a final microwave-assisted electrocyclization of the thus formed 6π-electron aza-triene system. |
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