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Biomimetic Total Syntheses of Amorfrutins A, B, ( S )‐D and ( R )‐D and Formal Synthesis of Amorfrutin C
Author(s) -
Mies Thomas,
Patel Calum,
Parsons Philip J.,
Barrett Anthony G. M.
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100301
Subject(s) - chemistry , total synthesis , polyketide , regioselectivity , allylic rearrangement , stereochemistry , bibenzyl , acylation , formal synthesis , terpene , biomimetic synthesis , combinatorial chemistry , organic chemistry , catalysis , biosynthesis , enzyme
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.