[Image: see text] The total synthesis of the complex pyrrole–imidazole alkaloids (±)–massadine and (±)–massadine chloride is described using a carefully orchestrated sequence of manipulations on highly polar and structurally complex intermediates. Key to the completion of this synthetic endeavor was the exploration of a unique and chemoselective method to oxidize unprotected guanidines under aqueous conditions in air. This oxidation has been optimized and applied to a selection of spirocyclic guanidines of varying complexity. Additionally, the 3,7–epi analogues of these interesting natural products have been synthesized and fully characterized.
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Su et al. (2008) studied this question.
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