Synthesis of natural maleimides farinomaleins C-E and evaluation of their antifungal activity

TETRAHEDRON LETTERS

卷:55

Article

Lahore, Santosh¹  Aiwale, Sachin T.¹  Sardi, Paola²  Dallavalle, Sabrina¹ 

[1] Univ Milan, Dept Food Environm & Nutr Sci, Div Chem & Mol Biol, I-20133 Milan, Italy

[2] Univ Milan, Dept Food Environm & Nutr Sci, Agroenvironm Sci Div, I-20133 Milan, Italy

关键词: Farinomaleins;    Maleimides;    Antifungal activity;    Synthesis;    Natural products;   

DOI  :  10.1016/j.tetlet.2014.05.023

来源: Elsevier

【 摘 要 】

A practical and convenient synthesis of naturally occurring farinomaleins C-E was achieved starting from readily available ethyl 3-methyl-2-oxobutyrate and triethyl phosphonoacetate. The key steps of the sequence included a Horner-Wadsworth-Emmons condensation to obtain the precursor farinomalein A and coupling with suitable alcohols to install the chain. The synthesis of farinomalein D has been achieved starting from (R)-isopropylideneglycerol on the basis of which the S configuration was assigned to the natural compound. The antifungal activity of the synthesized compounds was evaluated against Cladosporium cladosporioides. (C) 2014 Elsevier Ltd. All rights reserved.

【 授权许可】

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