Biomimetic synthesis of Sinularia meroterpenoids and photochemical reactivity of capillobenzopyranol
Biomimetic synthesis of Sinularia meroterpenoids and photochemical reactivity of capillobenzopyranol
Motivated by a biosynthetic proposal which suggests a chemical relationship between capilloquinol and capillobenzopyranol, our studies report the first synthesis of their probable biogenetic precursors, furanoquinol and furanoquinone. A bioinspired cascade using an ortho-quinone methide intermediate derived from furanoquinone was attempted to construct the spirocyclic moiety of capilloquinol but instead led to the formation of capillobenzopyranol via an oxa-6π-electrocyclisation. Subsequent photochemical transformations of capillobenzopyranol resulted in a formal 1,3-hydrogen shift followed by intramolecular [2 + 2]-cycloaddition to construct an unusual 6–6–6–4 fused polycyclic compound.
French, Sarah A.
29dd7b5c-5bf1-4330-895e-eeacdd858b0b
Peralta, Ricardo A.
114c10af-f8ad-49e0-9027-5066aab0d8ac
George, Jonathan H.
004df70b-45c3-479c-a9ee-48d328ef20c4
French, Sarah A.
29dd7b5c-5bf1-4330-895e-eeacdd858b0b
Peralta, Ricardo A.
114c10af-f8ad-49e0-9027-5066aab0d8ac
George, Jonathan H.
004df70b-45c3-479c-a9ee-48d328ef20c4
French, Sarah A., Peralta, Ricardo A. and George, Jonathan H.
(2025)
Biomimetic synthesis of Sinularia meroterpenoids and photochemical reactivity of capillobenzopyranol.
Organic and Biomolecular Chemistry.
(doi:10.1039/d5ob01430a).
Abstract
Motivated by a biosynthetic proposal which suggests a chemical relationship between capilloquinol and capillobenzopyranol, our studies report the first synthesis of their probable biogenetic precursors, furanoquinol and furanoquinone. A bioinspired cascade using an ortho-quinone methide intermediate derived from furanoquinone was attempted to construct the spirocyclic moiety of capilloquinol but instead led to the formation of capillobenzopyranol via an oxa-6π-electrocyclisation. Subsequent photochemical transformations of capillobenzopyranol resulted in a formal 1,3-hydrogen shift followed by intramolecular [2 + 2]-cycloaddition to construct an unusual 6–6–6–4 fused polycyclic compound.
Text
=d5ob01430a
- Version of Record
More information
Accepted/In Press date: 29 October 2025
e-pub ahead of print date: 21 November 2025
Additional Information:
Publisher Copyright:
This journal is © The Royal Society of Chemistry 2025
Identifiers
Local EPrints ID: 507180
URI: http://eprints.soton.ac.uk/id/eprint/507180
ISSN: 1477-0520
PURE UUID: be62b6f8-2085-4cdf-a2bf-0373551231ba
Catalogue record
Date deposited: 28 Nov 2025 17:38
Last modified: 29 Nov 2025 03:08
Export record
Altmetrics
Contributors
Author:
Sarah A. French
Author:
Ricardo A. Peralta
Author:
Jonathan H. George
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics