Biosynthetically-inspired oxidations of capillobenzopyranolElectronic supplementary information (ESI) available: NMR spectra for all new compounds. See DOI: 10.1039/c7ob00868f

The synthesis of verrubenzospirolactone from its proposed biosynthetic precursor, capillobenzopyranol, has been shown to be chemically feasible via a simple reaction sequence. The key steps are a chemoselective furan oxidation mediated by NaClO 2 , a stereoselective dehydration of a γ-methoxybutenol...

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Main Authors: Pepper, Henry P, Lam, Hiu C, George, Jonathan H
Format: Article
Language:English
Online Access:Get full text
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Summary:The synthesis of verrubenzospirolactone from its proposed biosynthetic precursor, capillobenzopyranol, has been shown to be chemically feasible via a simple reaction sequence. The key steps are a chemoselective furan oxidation mediated by NaClO 2 , a stereoselective dehydration of a γ-methoxybutenolide, and an intramolecular Diels-Alder reaction. The marine sponge meroterpenoid capillobenzopyranol has been converted into the co-isolated verrubenzospirolactone using simple and selective chemical transformations.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob00868f