Spiroaminal Model Systems of the Marineosins with Final Step Pyrrole Incorporation

Joseph D Panarese; Leah C Konkol; Cynthia B Berry; Brittney S Bates; Leslie N Aldrich; Craig W Lindsley

doi:10.1016/j.tetlet.2013.02.059

Spiroaminal Model Systems of the Marineosins with Final Step Pyrrole Incorporation

Tetrahedron Lett. 2013 May 1;54(18):2231-2234. doi: 10.1016/j.tetlet.2013.02.059.

Authors

Joseph D Panarese¹, Leah C Konkol, Cynthia B Berry, Brittney S Bates, Leslie N Aldrich, Craig W Lindsley

Affiliation

¹ Department of Chemistry, Vanderbilt University, Nashville, TN 37232, USA ; Department of Pharmacology, Vanderbilt Center for Neuroscience Drug Discovery, Vanderbilt Specialized Chemistry Center (MLPCN), Vanderbilt University Medical Center, Nashville, TN 37232, USA.

Abstract

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 (R)- or (S)-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.

Keywords: alkaloid; enantioselective; iminium triflate; marineosin; pyrrole.

Abstract

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