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Spiroaminal Model Systems of the Marineosins with Final Step Pyrrole Incorporation.

Panarese JD, Konkol LC, Berry CB, Bates BS, Aldrich LN, Lindsley CW
Tetrahedron Lett. 2013 54 (18): 2231-2234

PMID: 23606772 · PMCID: PMC3627418 · DOI:10.1016/j.tetlet.2013.02.059

In this Letter, we describe a short, 6-step enantioselective route to spiroaminal lactam model systems reminiscent of marineosins A and B has been developed starting from either ()- or ()-hydroxysuccinic acid, respectively, in ~9% overall yield. This route enables late stage incorporation of the pyrrole ring at C5 via nucleophilic displacement of an iminium triflate salt.

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