THE STRUCTURE OF CLEOMEOLIDE, AN UNUSUAL BICYCLIC DITERPENE FROM CLEOME VISCOSA L. (CAPPARACEAE)

Article abstract of DOI:10.1016/0040-4020(80)88044-6

A bicyclic diterpene cleomeolide (1), C20H30O3, has been isolated from Cleome viscosa L. (Capparaceae), and its stereostructure established by chemical, spectral and X-ray crystallographic means.Crystals of 1 belong to space group P2₁, with a=10.329(2)A, b=12.468(3)A, c=7.356(2)A, β=109.98 deg and Z=2.The structure was solved by a multiple solution procedure and refined by full matrix least-squares to give R=0.041 and wR=0.051.Oxidation of 1 gave the ketone 4, which on treatment with methanolic KOH led to a facile transannular reaction to give the lactone 6.