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Biomimetic Syntheses of Amorfrutin C and C ‐5 Substituted Amorfrutin Analogues
Author(s) -
Patel Calum,
Mies Thomas,
White Andrew J. P.,
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.202001487
Subject(s) - chemistry , prenylation , aldehyde , claisen rearrangement , alcohol , biomimetic synthesis , lithium (medication) , stereochemistry , catalysis , organic chemistry , enzyme , medicine , endocrinology
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.