Biosynthetically-inspired oxidations of capillobenzopyranol
Henry P Pepper1, Hiu C Lam, Jonathan H George
1Department of Chemistry, University of Adelaide, Adelaide, SA 5005, Australia. jonathan.george@adelaide.edu.au.
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.
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