The Stereochemical Structures of the Furanosesquiterpenoidal β-Hydroxy Ketones from the Myoporaceae

Abstract

Four furanosesquiterpene β-hydroxy ketones previously isolated from Myoporum spp., and given tentative names, are now assigned complete stereostructures from n.m.r. and X-ray data. The compounds are (5R,7R,9S)-9-hydroxy-5,9-dihydromyomontanone (Woogaroo) (1a), (5S,7R,9R)-9-hydroxy-5,9-dihydro- myomontanone (Redbank) (1b), (5R,7R,9R)-9-hydroxy-5,9-dihydromyomontanone (Perillup) (1c) and (4S,7S,8R)-4-hydroxy-10,11-didehydro-4,8-dihydromyodesmone (Carney's ketol) (2a). The stereo- structures of two other previously reported compounds, Kindon ketol ((4S,7S,8R)-4-hydroxy-4,8- dihydromyodesmone) (2b), and Carr's ketol ((4S,7S,8S)-4-hydroxy-4,8-dihydromyodesmone) (2c), follow from the above results.