We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Biomimetic Total Syntheses of Amorfrutins A, B, (S)-D and (R)-D and Formal Synthesis of Amorfrutin C.
- Authors
Mies, Thomas; Patel, Calum; Parsons, Philip J.; Barrett, Anthony G. M.
- 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.
- Subjects
BIOMIMETIC synthesis; AROMATIZATION; NATURAL products; TERPENES; PALLADIUM
- Publication
European Journal of Organic Chemistry, 2021, Vol 2021, Issue 17, p2540
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202100301