Department of Chemistry, Simon Fraser University, Burnaby, V5A 1S6, BC (Canada), Fax: (+1) 1-778-782-3765.
Chemistry. 2013 Sep 16;19(38):12649-52. doi: 10.1002/chem.201302352. Epub 2013 Aug 19.
Structural reassignment: A total synthesis of the proposed structure of (-)-laurefurenyne A has been accomplished that relies on organocatalytic aldehyde α-chlorination and a flexible chlorohydrin-based strategy for stereocontrolled access to the bis-tetrahydrofuran core of the natural product. Analysis of incongruities between the (1) H NMR spectra of synthetic and natural material led to a configurational reassignment for the natural product, which was also confirmed by total synthesis.
(-)-laurefurenyne A 的提议结构的全合成已经完成,该合成依赖于有机催化的醛 α-氯化和灵活的氯醇基策略,用于立体控制进入天然产物的双四氢呋喃核心。对合成和天然材料的(1)H NMR 光谱之间的不协调性进行分析,导致对天然产物的构型重排,这也通过全合成得到了证实。