Biomimetic Total Syntheses of Amorfrutins A, B, ( S )‐D and ( R )‐D and Formal Synthesis of Amorfrutin C | Zendy

Mies Thomas | Zendy; Patel Calum | Zendy; Parsons Philip J. | Zendy; Barrett Anthony G. M. | Zendy

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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.

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