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Tetrahedron Lett. 2013 May 1;54(18):2231-2234.

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

Author information

  • 1Department 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

PMID:
23606772
[PubMed]
PMCID:
PMC3627418
Free PMC Article
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