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Biosynthetically-inspired oxidations of capillobenzopyranol

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Abstract

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 NaClO2, a stereoselective dehydration of a γ-methoxybutenolide, and an intramolecular Diels–Alder reaction.

Graphical abstract: Biosynthetically-inspired oxidations of capillobenzopyranol

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Publication details

The article was received on 07 Apr 2017, accepted on 09 May 2017 and first published on 15 May 2017


Article type: Paper
DOI: 10.1039/C7OB00868F
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Biosynthetically-inspired oxidations of capillobenzopyranol

    H. P. Pepper, H. C. Lam and J. H. George, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00868F

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