Organic Letters 2009-06-18

Biomimetically inspired short access to the 2-aminoimidazole-fused tetracyclic core of (+/-)-dibromoagelaspongin.

Sylvain Picon, Huu Dau Elise Tran, Marie-Thérèse Martin, Pascal Retailleau, Anne Zaparucha, Ali Al-Mourabit

Index: Org. Lett. 11(12) , 2523-6, (2009)

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Abstract

A six-step synthesis of the tetracyclic core of the natural compound (+/-)-dibromoagelaspongin, isolated from Agelas sp. Sponge, was achieved from the commercially available 5-aminopentan-1-ol, 2-trichloroacetylpyrrole, and 2-aminopyrimidine. Following a biomimetic inspired approach, successive oxidative reactions including the final DMDO biomimetic oxidation gave the interesting triaminomethane-fused core.