Total syntheses of isonaamine C and isonaamidine E

TETRAHEDRON LETTERS

卷:52

Article

Lima, Heather M.¹  Garcia-Barboza, Beatriz J.¹  Khatibi, Nicole N.¹  Lovely, Carl J.¹ 

[1] Univ Texas Arlington, Dept Chem & Biochem, Arlington, TX 76019 USA

关键词: Leucetta;    2-Aminoimidazole;    4,5-Diiodoimidazole;    Azidation;    Methylparabanic acid;   

DOI  :  10.1016/j.tetlet.2011.08.030

来源: Elsevier

【 摘 要 】

The total syntheses of two alkaloids isolated from a marine sponge of the Leucetta sp. have been accomplished in 6 and 7 steps starting from a 4,5-diiodoimidazole derivative. Grignard mediated halogen-metal exchange was used to install the benzyl side chain. C2 substitution was accomplished via lithiation followed by quenching with trisyl azide which provided isonaamine C after hydrogenation. Isonaamidine E was then prepared from isonaamine C via introduction of the hydantoin ring by reaction with an activated parabanic acid derivative. (C) 2011 Elsevier Ltd. All rights reserved.

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