The structures of the two bisindole alkaloids named in the title were elucidated. Acid-catalyzed condensation of natural voacangine with vobasinol prepared from natural vobasine yielded voacamine and voacamidine. Analogous condensation of voacangarine with vobasinol furnished synthetic voacorine.Recent investigations of the genus Vo canga have unearthed a quantity of new alkaloids biogenetically derived from tryptophan. One series of natural bases is characterized structurally by the presence of an isoquinuclidine ring and voacangine4 (1) is the prototype of the entire group. Vobasine5 ( 3) is representative of a second class of alkaloids containing the characteristic 2acylindole grouping. Because of their apparent dimeric nature, a series of structurally unknown substances was classed together in a third family.Voacamine, a prominent member of this group of "dimeric" Voacanga alkaloids, was first isolated from Voacanga africana Stapf,6-7 and subsequently from other species6,8 and other genera.910 Its ultraviolet spectrum (X®'°H 225, 287, and 294 µ] e 52,600, 17,850, and 19,950) suggested the presence of a 5-methoxyindole chromophore and an equivalent weight of 698, obtained by potentiometric titration,11 confirmed the "dimeric" nature of voacamine. Two of the four nitrogen atoms were found to be tertiary and basic (p = 5.19 and 6.78),11 whereas the remaining two were readily assigned as components of two indole rings. Early investiga-tors12,13 established the presence of one methoxy, one N-methyl, and two carbomethoxy groups in the molecule. Potash fusion of voacamine produced trimethylamine and 3-ethyl-5-methylpyridine, the latter being a characteristic transformation product of pentacyclic indole alkaloids containing the voacangine (1) skeleton. Saponification of voacamine furnished a salt of a dicarboxylic acid which on esterification with methanolic hydrochloric acid gave decarbomethoxy-epr-voacamine (17). Esterification with diazomethane yielded ept-voacamine (15)11 which could also be obtained directly from voacamine by sodiumm ethoxide catalyzed epimerization.The facile monodecarboxylation of the dicarboxylic acid, coupled with the aforementioned degradation to
The extensive literature on organizational wrongdoing tends to assume that a clear red line divides the moral terrain. However, many organizations function not as moral orders, but as moral pursuits in which there is intentionally no explicit definition of right and wrong; members are encouraged to engage in an ongoing pursuit of personal morality. We use illustrations from field sites in which red lines proved either well-defined or elusive to theorize differences in forms of wrongdoing in moral orders versus moral pursuits. More specifically, we explore cases in which organizational actors seek to (re)define right and wrong and to pursue actions that they consider moral, but that others in their setting consider wrongdoing. We identify two sets of misaligned moral strategies: one involving moral hijacking, moral assembling, and moral blurring that occurs when individuals engage in a moral pursuit from within the context of a moral order; and another involving moral circumscribing, moral spotlighting, and moral seceding that occurs when individuals seek to establish a moral order from within a moral pursuit. We develop this typology to highlight the importance of context in defining wrongdoing, and to better understand the variety of wrongdoing in organizations.
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