(2aR*,5S*,6aS*,8aS*,E)-Ethyl 5-hy-droxy-7,7,8a-trimethyl-8-oxo-2,2a,6,6a,7,8,8a,8b-octa-hydro-1H-penta-leno[1,6-bc]oxepine-4-carboxyl-ate

Acta Crystallogr Sect E Struct Rep Online. 2012 Dec 1;68(Pt 12):o3392-3. doi: 10.1107/S1600536812046776. Epub 2012 Nov 24.

Abstract

The title compound, C17H24O5, featuring a 2-carbeth-oxy-3-oxepanone unit in its intra-molecularly O-H⋯O hydrogen-bonded enol form, was obtained via [(CF3CO2)2Rh]2-catal-ysed intra-molecular O-H bond insertion in the α-diazo-ω-hy-droxy-β-ketoester, ethyl 4-[(1S,3aS,6R,6aS)-6-hy-droxy-2,2,3a-trimethyl-3-oxo-octa-hydro-penta-len-1-yl]-2-diazo-3-oxobutano-ate. The seven-membered oxacyclic ring, thus constructed on a cis-fused diquinane platform, was found to adopt a distorted boat-sofa conformation.