Department of Chemistry , University of Oxford , Chemistry Research Laboratory, Mansfield Road , Oxford OX1 3TA , U.K.
Department of Oncology , University of Oxford , Old Road Campus Research Building, Roosevelt Drive Oxford OX3 7DQ , U.K.
Org Lett. 2018 Jun 15;20(12):3583-3586. doi: 10.1021/acs.orglett.8b01370. Epub 2018 Jun 4.
A short (10 step) and efficient (15% overall yield) synthesis of the natural product (-)-(3 R)-inthomycin C is reported. The key steps comprise three C-C bond-forming reactions: (i) a vinylogous Mukaiyama aldol, (ii) an olefin cross-metathesis reaction, and (iii) an asymmetric Mukaiyama-Kiyooka aldol. This route is notable for its brevity and has the advantage of lacking stoichiometric tin-promoted cross-coupling reactions present in previous approaches. Initial investigations on the biological activity of (-)-(3 R)-inthomycin C and structural analogues on human cancer cell lines are also described for the first time.
本文报道了天然产物（-）-（3R）-因替霉素 C 的一种简短（10 步）、高效（总收率 15%）的合成方法。关键步骤包括三个 C-C 键形成反应：（i）烯醇式 Mukaiyama 醛缩合反应，（ii）烯烃交叉复分解反应，以及（iii）不对称 Mukaiyama-Kiyooka 醛缩合反应。该路线的显著特点是简短，并且具有避免了前一种方法中存在的大量锡促进交叉偶联反应的优点。本文还首次描述了（-）-（3R）-因替霉素 C 及其结构类似物对人癌细胞系的生物活性的初步研究。
