Synthesis of the unique angular tricyclic chromone structure proposed for aspergillitine, and its relationship with alkaloid TMC-120B

SO Simonetti, EL Larghi, ABJ Bracca…

Index: Simonetti, Sebastian O.; Larghi, Enrique L.; Bracca, Andrea B. J.; Kaufman, Teodoro S. Organic and Biomolecular Chemistry, 2012 , vol. 10, # 20 p. 4124 - 4134

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Citation Number: 17

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-Bu3SnCH2CHCH2, followed by double bond isomerization, oximation of ...