Glycosidic Disecoeudesmanolides and Other Secosesquiterpene Lactones from Picradeniopsis Species. X-ray Analysis of Bahia I

Article abstract of DOI:10.1021/jo01304a005

The unusual disecoeudesmanolide glycosides 3a and 5a were isolated from an Arizona collection of Picradeniopsis woodhousei (Gray) Rydb. in addition to the heliangolide woodhousin (8a) and the flavone jaceidin.P.woodhousei from New Mexico gave the secoeudesmanolide precursor 7a of 3a and 5a, the woodhousin analogue 8c, the guaianolide 9, and the secoheliangolide 11a.The structures were determined by chemical transformations and spectroscopic means.Eucannabinolide (13) and bahia II (14b) were isolated from Picradeniopsis oppositifolia (Nutt.) Rydb.The stereochemistries of 14b and its congeners bahia I and bahifolin were settled by X-ray analysis of bahia I (14a).