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  • Title: Synthesis of the unique angular tricyclic chromone structure proposed for aspergillitine, and its relationship with alkaloid TMC-120B.
    Author: Simonetti SO, Larghi EL, Bracca AB, Kaufman TS.
    Journal: Org Biomol Chem; 2012 May 28; 10(20):4124-34. PubMed ID: 22531888.
    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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