Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique, Palaiseau Cedex 91128 Cedex, France.
Org Lett. 2022 Dec 30;24(51):9370-9374. doi: 10.1021/acs.orglett.2c03671. Epub 2022 Dec 19.
A versatile strategy to access vicinally functionalized cyclopentanones and cyclohexanones is described. It takes advantage of new reagents, α-xanthyl enones, which can be prepared from the reaction of xanthate salts with the corresponding epoxyketones under mild conditions. β-Functionalization of these compounds can be performed by conjugate additions without affecting the xanthate moiety. This significantly expands the pool of xanthate substrates, allowing the synthesis of open chain and fused bicyclic building blocks useful in the synthesis of natural products.
本文描述了一种获得邻位官能化的环戊酮和环己酮的通用策略。它利用了新的试剂α-蒽酮烯酮，这些试剂可以在温和的条件下通过黄原酸盐与相应的环氧化酮反应制备。这些化合物的β-官能化可以通过共轭加成来进行，而不会影响黄原酸酯部分。这大大扩展了黄原酸酯底物的范围，允许合成在天然产物合成中有用的开链和稠合双环砌块。
