| A strategy was devised for the efficient synthesis of natural product groups based on their structure and possible biosynthetic origins. Using simple, biologically plausible, transformations this strategy was applied to the pyridoacridine and euthyroideone natural product classes. A partial synthesis of euthyroideone A (1) incorporating two new reactions was accomplished. A one-step total synthesis of the styelsamine B ( 40) from N-acetyl dopamine was achieved in 35% yield. The further elaboration of this pyridoacridine to other related compounds was then demonstrated. Syntheses for all dopamine-derived pyridoacridines were proposed based on a mapping strategy developed for this purpose. |
