使用二氧化锍选择性合成缬氨霉素的羟基类似物。
Selective synthesis of hydroxy analogues of valinomycin using dioxiranes.
机构信息
Dipartimento Chimica, Università di Bari A. Moro, v. Amendola 173, 70126 Bari, Italy.
出版信息
Org Lett. 2011 Oct 7;13(19):5096-9. doi: 10.1021/ol201971v. Epub 2011 Sep 12.
Abstract
A synthesis of representative monohydroxy derivatives of valinomycin (VLM) was achieved under mild conditions by direct hydroxylation at the side chains of the macrocyclic substrate using dioxiranes. Results demonstrate that the powerful methyl(trifluoromethyl)dioxirane 1b should be the reagent of choice to carry out these key transformations. Thus, a mixture of compounds derived from the direct dioxirane attack at the β-(CH(3))(2)C-H alkyl chain of one Hyi residue (compound 3a) or of one Val moiety (compounds 3b and 3c) could be obtained. Following convenient mixture separation, each of the new oxyfunctionalized macrocycles became completely characterized.
摘要
在温和条件下，通过使用二氧化锍在大环底物的侧链上直接羟化，实现了缬氨霉素（VLM）的代表性单羟基衍生物的综合。结果表明，强大的甲基（三氟甲基）二氧杂环戊烷 1b 应该是进行这些关键转化的首选试剂。因此，可以获得直接二氧化锍攻击一个 Hyi 残基的β-（CH(3))(2)C-H 烷基链（化合物 3a）或一个 Val 部分（化合物 3b 和 3c）的化合物的混合物。在方便地进行混合物分离后，每个新的含氧功能化大环都得到了完全表征。
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