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Biomimetic total syntheses of amorfrutins A, B, (S)-D and (R)-D and formal synthesis of amorfrutin C

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

Abstract

Bibenzyl natural products, such as the amorfrutins, contain a heavily substituted aromatic core and display a diverse range of biological activities (anti-tumor, anti-diabetic, antimicrobial, and antibiotic). In this study, we report unified syntheses of amorfrutin A to D either through total or formal synthesis by employing a dual biomimetic strategy of polyketide aromatization followed by remote terpene functionalization. The key core structures were synthesized from β-keto dioxinone esters through a magnesium(II) mediated regioselective C-acylation, palladium catalyzed decarboxylative allylic rearrangement, and dehydrative cyclization.

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