Issue 22, 2017

Biosynthetically-inspired oxidations of capillobenzopyranol

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

Supplementary files

Article information

Article type
Paper
Submitted
07 Apr 2017
Accepted
09 May 2017
First published
15 May 2017

Org. Biomol. Chem., 2017,15, 4811-4815

Biosynthetically-inspired oxidations of capillobenzopyranol

H. P. Pepper, H. C. Lam and J. H. George, Org. Biomol. Chem., 2017, 15, 4811 DOI: 10.1039/C7OB00868F

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