Spiroaminal model systems of the marineosins with final step pyrrole incorporation

TETRAHEDRON LETTERS

卷:54

Article

Panarese, Joseph D.^1,2  Konkol, Leah C.^1,2  Berry, Cynthia B.¹  Bates, Brittney S.¹  Aldrich, Leslie N.¹  Lindsley, Craig W.^1,2 

[1] Vanderbilt Univ, Dept Chem, Nashville, TN 37232 USA

[2] Vanderbilt Univ, Dept Pharmacol, Vanderbilt Ctr Neurosci Drug Discovery, Vanderbilt Specialized Chem Ctr MLPCN,Med Ctr, Nashville, TN 37232 USA

关键词: Marineosin;    Iminium triflate;    Enantioselective;    Pyrrole;    Alkaloid;   

DOI  :  10.1016/j.tetlet.2013.02.059

来源: Elsevier

【 摘 要 】

In this Letter, we describe a short, six step enantioselective route to spiroaminal lactam model systems reminiscent of marineosins A and B that has been developed starting from either (R)- or (S)-hydroxysuccinic acid, respectively, in similar to 9% overall yield. This route enables late stage incorporation of the pyrrole ring at C5 via nucleophilic displacement of an iminium triflate salt. (C) 2013 Elsevier Ltd. All rights reserved.

【 授权许可】

Free