DiBello Mikaela, Xu Zhi, Palazzo Alexandria M, Herzon Seth B
Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
Departments of Pharmacology and Therapeutic Radiology, Yale School of Medicine, New Haven, Connecticut 06520, United States.
Org Lett. 2025 Jan 31;27(4):937-941. doi: 10.1021/acs.orglett.4c04098. Epub 2025 Jan 23.
We describe a stereoselective synthesis of the dimeric diazofluorene , a potential precursor to the cytotoxic -symmetric bacterial metabolite (-)-lomaiviticin A (). An efficient route was developed to convert the tetracyclic diol to the diketone (five steps, 30% overall). Oxidative dimerization of the enoxysilane provided the -symmetric dimeric diazofluorene in 56% yield and with 15:1:0 diastereoselectivity. Deprotection and 2D NMR analysis indicated that the major diastereomer possessed the (2,2') configuration found in . This approach may ultimately be useful in the synthesis of itself.
我们描述了二聚重氮芴的立体选择性合成，它是具有细胞毒性的对称细菌代谢物（-）-洛迈维替菌素A（）的潜在前体。开发了一条有效的路线，将四环二醇转化为二酮（五步，总产率30%）。烯oxysilane的氧化二聚反应以56%的产率和15:1:0的非对映选择性提供了对称的二聚重氮芴。脱保护和二维核磁共振分析表明，主要的非对映异构体具有在中发现的（2,2'）构型。这种方法最终可能对本身的合成有用。
