Bioinspired Total Synthesis of Hyperireflexolides A and B
Date
2023
Authors
zur Bonsen, A.B.
Sumby, C.J.
George, J.H.
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Journal article
Citation
Organic Letters, 2023; 25(34):6317-6321
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Andreas B. zur Bonsen, Christopher J. Sumby, and Jonathan H. George
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Abstract
Hyperireflexolides A and B were synthesized in six steps via the dearomatization and fragmentation of a simple acylphloroglucinol starting material. The dearomatized acylphloroglucinol undergoes a sequence of oxidative radical cyclization, retro-Dieckmann fragmentation, stereodivergent intramolecular carbonyl-ene reactions, and final α-hydroxy-β-diketone rearrangements to give the target natural products. This sequence is based on a biosynthetic proposal that claims the hyperireflexolides as highly rearranged polycyclic polyprenylated acylphloroglucinols (PPAPs), which is supported by the structural revision of hyperireflexolide B.
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Published: August 22, 2023
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© 2023 American Chemical Society