The Molecular Structures of Browniine Perchlorate and Dictyocarpine-Acetone Complex

Abstract

Browniine perchlorate crystallizes in the monoclinic space group P2V The structure was solved by multisolution methods and refined to an R of 0.078 for 2766 observed reflections. Dictyocarpine crystallizes from acetone as an acetone complex. The crystals are orthorhombic, space group P212121. The structure was solved by multisolution methods and refined to an R of 0.085 for 2483 observed reflections. These structural results require the configuration of the C(l)-methoxyl group in all C19-diterpenoid alkaloids related to lycoctonine to be revised from ß to a.Recently, we described the methylation of delsoline (1) with methyl iodide and sodium hydride to give the known alkaloid dephatine (2) (1). Because the a-configuration of the C(7)-hydroxyl group in delsoline is well established by chemical (2) and spectral data (3), we pointed out that delphatine must also bear a C( 1 )-ot-methoxyl