Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, U.K.
Sezione Chimica Generale e Organica "A. Marchesini", Università degli Studi di Milano, Via G. Venezian 21, 20133 Milano, Italy.
Org Lett. 2021 Oct 1;23(19):7439-7444. doi: 10.1021/acs.orglett.1c02650. Epub 2021 Sep 8.
The stambomycins are a family of bioactive macrolides isolated from . Aside from two stereocenters installed through cytochrome P450 oxidations, their stereochemistry has been predicted by sequence analysis of the polyketide synthase. We report a synthesis of the C1-C27 fragment of stambomycin D, the spectroscopic data of which correlates well with that of the natural product, further validating predictive sequence analysis as a powerful tool for stereochemical assignment of complex polyketide natural products.
链霉菌素有一组生物活性的大环内酯类化合物,从链霉菌属中分离得到。除了通过细胞色素 P450 氧化作用安装的两个手性中心外,其立体化学结构已通过聚酮合酶的序列分析进行了预测。我们报告了链霉菌素 D 的 C1-C27 片段的合成,其光谱数据与天然产物非常吻合,进一步验证了预测序列分析是一种用于复杂聚酮天然产物立体化学分配的有力工具。