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Biomimetic syntheses of amorfrutin C and C-5 substituted amorfrutin analogues

Authors
  • Patel, C
  • Mies, T
  • White, AJP
  • Parsons, PJ
  • Barrett, AGM
Publication Date
Jan 01, 2021
Source
Spiral - Imperial College Digital Repository
Keywords
License
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Abstract

Amorfrutin C, a C-5 prenyl amorfrutin, its allyl analog and an amorfrutin C-5 aldehyde have been synthesized using a biomimetic strategy from non-aromatic precursors. In this approach, a dioxinone derived β,δ-diketo ester underwent a decarboxylative Pd(0) catalyzed prenyl migration to give a β,δ-diketo dioxinone, which readily aromatized giving the amorfrutin core. The introduction of prenyl and allyl moieties at the C-5 position of the scaffold was accomplished using a Claisen rearrangement. Alternatively, iodination, lithium-iodine exchange and trapping with DMF gave the amorfrutin aldehyde and an amorfrutin alcohol when excess n-BuLi was used.

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