Tetrahedron letters

Synthesis of non-THF analogs of acetogenin toward simplified mimics

…, N Ichimaru, M Abe, M Murai, T Hamada, T Nishioka…

Index: Fujita, Daisuke; Ichimaru, Naoya; Abe, Masato; Murai, Masatoshi; Hamada, Takeshi; Nishioka, Takaaki; Miyoshi, Hideto Tetrahedron Letters, 2005 , vol. 46, # 34 p. 5775 - 5779

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Citation Number: 19

Abstract

Acetogenin analogs in which the bis-adjacent THF ring was replaced with an enantioselectively synthesized 1, 2-cyclopentanediol bis-ether skeleton were synthesized to obtain simplified mimics, and their inhibitory effect on mitochondrial NADH–ubiquinone oxidoreductase (complex I) was examined. The results clearly demonstrate that the 1, 2- cyclopentanediol bis-ether motif can substitute for the bis-THF ring while maintaining very ...