University of Michigan , Department of Chemistry, Willard Henry Dow Laboratory, 930 North University Avenue, Ann Arbor, Michigan 48109, United States.
Org Lett. 2016 Mar 18;18(6):1310-3. doi: 10.1021/acs.orglett.6b00254. Epub 2016 Mar 2.
A mild, catalytic method for the synthesis of 3,4-dihydro-2H-pyrans is described. The FeCl3-catalyzed transformation of aryl- and alkyl β-diketones enables synthetic access to functionalized pyran core structures incorporated in many natural products and biologically active target structures. The method represents a mild alternative to currently available reaction protocols relying on stoichiometric reagents and harsh reaction conditions. This FeCl3-catalyzed transformation has enabled the selective synthesis of α-lapachone in two synthetic transformations and subsequently β-lapachone in three synthetic transformations, which is currently undergoing clinical trials as a potent anticancer agent.
描述了一种温和的、催化合成 3,4-二氢-2H-吡喃的方法。FeCl3 催化的芳基和烷基β-二酮的转化为许多天然产物和生物活性靶结构中包含的功能化吡喃核心结构的合成提供了途径。该方法是目前依赖于化学计量试剂和苛刻反应条件的现有反应方案的温和替代方案。这种 FeCl3 催化转化已能够在两种合成转化中选择性地合成α-拉帕酮，随后在三种合成转化中合成β-拉帕酮，目前正在作为一种有效的抗癌剂进行临床试验。
