A synthetic investigation into the biosynthesis of hypsampsone A
A synthetic investigation into the biosynthesis of hypsampsone A
A simplified proposal for the biogenetic origin of hypsampsone A, a complex meroterpenoid, is supported by a bioinspired cascade reaction that rapidly assembles its polycyclic core. The key steps in both the proposed biosynthesis and the bioinspired cascade are a spontaneous intramolecular carbonyl-ene reaction, an α-hydroxy- β-diketone rearrangement and a terminating intramolecular aldol reaction. The feasibility of this model cascade reaction strongly suggests that hypsampsone A is a highly rearranged member of the polycyclic polyprenylated acylphloroglucinol (PPAP) family of natural products.
4671-4674
Jarman, Jhayden J.A.
f7f3a69b-a6b7-4520-82ff-d9b29062cf66
Zur Bonsen, Andreas B.
84aa53be-2426-4acd-81f2-d55eaff14825
George, Jonathan H.
004df70b-45c3-479c-a9ee-48d328ef20c4
23 April 2025
Jarman, Jhayden J.A.
f7f3a69b-a6b7-4520-82ff-d9b29062cf66
Zur Bonsen, Andreas B.
84aa53be-2426-4acd-81f2-d55eaff14825
George, Jonathan H.
004df70b-45c3-479c-a9ee-48d328ef20c4
Jarman, Jhayden J.A., Zur Bonsen, Andreas B. and George, Jonathan H.
(2025)
A synthetic investigation into the biosynthesis of hypsampsone A.
Organic and Biomolecular Chemistry, 23 (19), .
(doi:10.1039/d5ob00045a).
Abstract
A simplified proposal for the biogenetic origin of hypsampsone A, a complex meroterpenoid, is supported by a bioinspired cascade reaction that rapidly assembles its polycyclic core. The key steps in both the proposed biosynthesis and the bioinspired cascade are a spontaneous intramolecular carbonyl-ene reaction, an α-hydroxy- β-diketone rearrangement and a terminating intramolecular aldol reaction. The feasibility of this model cascade reaction strongly suggests that hypsampsone A is a highly rearranged member of the polycyclic polyprenylated acylphloroglucinol (PPAP) family of natural products.
Text
d5ob00045a (1)
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Accepted/In Press date: 21 April 2025
Published date: 23 April 2025
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© The Royal Society of Chemistry 2025.
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Local EPrints ID: 502296
URI: http://eprints.soton.ac.uk/id/eprint/502296
ISSN: 1477-0520
PURE UUID: c42b92b1-ac66-4233-8913-5099d1460146
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Date deposited: 20 Jun 2025 16:34
Last modified: 22 Aug 2025 02:43
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Contributors
Author:
Jhayden J.A. Jarman
Author:
Andreas B. Zur Bonsen
Author:
Jonathan H. George
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