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Total Synthesis and Biological Evaluation of Zealactone 1a/b
Helvetica Chimica Acta ( IF 1.5 ) Pub Date : 2020-03-23 , DOI: 10.1002/hlca.202000017
Masahiko Yoshimura 1 , Michael Dieckmann 2 , Pierre‐Yves Dakas 2 , Raymonde Fonné‐Pfister 2 , Claudio Screpanti 2 , Katrin Hermann 2 , Stefano Rendine 2 , Pierre Quinodoz 2 , Beyza Horoz 3 , Saron Catak 3 , Alain De Mesmaeker 2
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Strigolactones are plant hormones, which play pivotal roles in plant growth and development with potential application in sustainable agriculture. Recently, zealactone 1a/b has been identified as the major strigolactone from the root exudates of corn. Although zealactone is a promising molecule affecting signaling in the rhizosphere as well as in planta, evaluating its biological activities has been hampered by its low natural abundance and its relative chemical instability. Herein, we present the total synthesis of zealactone 1a/b based on our studies employing a [2+2]‐cycloaddition strategy and a chemoselective Baeyer‐Villiger oxidation to forge the γ‐butyrolactone fragment. Furthermore, we disclose the biological activities of zealactone 1a/b on corn and in soil in comparison with related synthetic analogues.

中文翻译:

玉米甾酮1a / b的全合成及生物学评价

内酯是植物激素,在植物生长发育中起关键作用,并在可持续农业中有潜在的应用。最近,从玉米根分泌物中鉴定出玉米甾酮1a / b是主要的硬皮内酯。尽管玉米黄酮是影响根际和植物中信号转导的有前途的分子,但其生物活性的评估因其低天然丰度和相对化学不稳定而受到阻碍。在此,我们根据[2 + 2]-环加成策略和化学选择性Baeyer-Villiger氧化法锻造γ的研究结果,给出了玉米黄酮1a / b的总合成丁内酯片段。此外,与相关的合成类似物相比,我们公开了玉米蛋白内酯1a / b在玉米和土壤中的生物活性。
更新日期:2020-03-23
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