Ramesh Karu, Bearne Stephen L
Department of Biochemistry & Molecular Biology, Dalhousie University, Halifax, Nova Scotia, B3H 4R2, Canada.
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H 4R2, Canada.
Beilstein J Org Chem. 2025 Aug 28;21:1730-1736. doi: 10.3762/bjoc.21.135. eCollection 2025.
Lipophilic yeasts of the genus are commensal fungi that constitute the normal skin microbiota but may become pathogenic. These fungi, especially , convert tryptophan into various alkaloid indoles such as malassezione, which may serve as virulence factors. To facilitate testing of malassezione as an aryl hydrocarbon receptor agonist and potential glucokinase activator, we developed a convenient synthetic route from commercially available indole-3-acetic acid. Treatment of the -Boc-protected indole-3-acetic acid with -ethyl-'-(3-dimethylaminopropyl)carbodiimide (EDC) in the presence of DMAP generates the ,'-Boc-protected malassezione, which upon deprotection yields malassezione in an overall yield of ca. 20%. This is an improvement over the preparation of the isonitrile followed by an Fe hydride initiated isonitrile-olefin intramolecular coupling reaction, which generated malassezione with an overall yield of ca. 5%. Furthermore, the present method may also be used to prepare related compounds.
属的亲脂性酵母是共生真菌，它们构成了正常的皮肤微生物群，但可能会致病。这些真菌，尤其是，将色氨酸转化为各种生物碱吲哚，如马拉色菌，其可能作为毒力因子。为了便于测试马拉色菌作为芳烃受体激动剂和潜在的葡萄糖激酶激活剂，我们从市售的吲哚-3-乙酸开发了一条简便的合成路线。在DMAP存在下，用 - 乙基 - '-(3 - 二甲基氨基丙基)碳二亚胺(EDC)处理 - Boc保护的吲哚-3-乙酸，生成，'-Boc保护的马拉色菌，脱保护后得到马拉色菌，总产率约为20%。这比先制备异腈然后进行氢化铁引发的异腈-烯烃分子内偶联反应制备马拉色菌有改进，后者总产率约为5%。此外，本方法还可用于制备相关化合物。
