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https://hdl.handle.net/2440/139346
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Type: | Journal article |
Title: | Bioinspired Total Synthesis of Hyperireflexolides A and B |
Author: | zur Bonsen, A.B. Sumby, C.J. George, J.H. |
Citation: | Organic Letters, 2023; 25(34):6317-6321 |
Publisher: | American Chemical Society (ACS) |
Issue Date: | 2023 |
ISSN: | 1523-7060 1523-7052 |
Statement of Responsibility: | Andreas B. zur Bonsen, Christopher J. Sumby, and Jonathan H. George |
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. |
Keywords: | Chemical synthesis; Fragmentation; Organic synthesis; Pharmaceuticals; Rearrangement |
Description: | Published: August 22, 2023 |
Rights: | © 2023 American Chemical Society |
DOI: | 10.1021/acs.orglett.3c02232 |
Grant ID: | http://purl.org/au-research/grants/arc/DP200102964 |
Published version: | http://dx.doi.org/10.1021/acs.orglett.3c02232 |
Appears in Collections: | Chemistry publications |
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