Arborinol methyl ether from Areca catechu L.

Abstract

The title compound isolated from Areca catechu L. (common name: arborinol methyl ether; a member of the arborane family) was established as 3-methoxyarbor-9(11)-ene, C31H52O. Rings A/B/C/D assume a chair conformation, while ring E has an envelope conformation. The absolute configuration was determined to be (3R,5R,8S,10S,13R,14S,17S,18S, 21S) by analysis of Bijvoet pairs based on resonant scattering of light atoms, yielding a Hooft parameter y of -0.03 (3).