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A concise synthesis of the tricyclic ketopyrrole segment of roseophilin is described in which key features include stereoselective conjugate addition to monosubstituted cyclopentenones, optimised conditions for the rearrangement of 1°-propargylic alcohols to vinyl ketones, 13-endo-trig free-radical macrocyclisation, and Paal–Knorr pyrrole condensation accompanied by oxidation in situ to complete the synthesis. Model studies on methylene oxidation α- to pyrrole rings are also described.
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Robertson et al. (2000) studied this question.
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