With the substrate scope inspected, a comprehensive series of experiments are performed to understand the reaction mechanism. An initial hint at the unusual nature of the catalytic process comes from an attempt at the isolation of catalytic intermediate (Scheme 3). A cobalt complex can indeed be isolated in catalysis involving 1a and 2a, albeit in small quantity (12% yield, calculated in reference to 2a), under the modified condition of 0. With the homeostatic catalysis products created herein, structural diversification and pharmaceutical agent manufacturing can be envisioned (Scheme 10). Indeed, rutheniumcatalyzed C-H bond activation in 3aa enables its coupling with 4 to yield 5. Starting from 3aw, schizocommunin (6), a fungal alkaloid that is cytotoxic against murine lymphoma cells by activating aryl hydrocarbon receptor gene battery, can be constructed by exploiting the nucleophilicity of methyl substituent. This nucleophilicity of methyl group also allows the use of 3aw in a threestep assembly of 7, a potent promoter of p53 activity in rhabdomyosarcoma. The methyl group can be rendered electrophilic by bromination for synthetic access to 8, an inhibitor of tubulin assembly that shows anti-proliferative activity against HT29 cell line. Another nucleophilic site on 3aw, N3, can be harnessed for the synthesis of an anti-inflammatory and analgesic drug, diproqualone (9).