Department of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.
J Am Chem Soc. 2021 Nov 24;143(46):19311-19316. doi: 10.1021/jacs.1c11117. Epub 2021 Nov 12.
Here we report the total synthesis of phainanoid A, a unique dammarane-type triterpenoid (DTT), using an unusual bidirectional synthetic strategy. It features two transition-metal-mediated highly diastereoselective transformations to access the two challenging strained ring systems that branch toward opposite directions from the tricyclic core. This work also highlights the strategic use of ketones (or enol triflates) as versatile handles for rapid growth of molecular complexity in all key transformations, which paves the way for efficient preparations of complex and biologically significant DTTs.
在这里，我们报告了使用一种不寻常的双向合成策略，对独特的达玛烷型三萜（DTT）菲烷酮 A 的全合成。它具有两个过渡金属介导的高度非对映选择性转化，以获得从三环核心向相反方向分支的两个具有挑战性的张力环系统。这项工作还突出了酮（或烯醇三氟甲磺酸酯）作为在所有关键转化中快速增加分子复杂性的通用手段的战略用途，为有效制备复杂和具有生物学意义的 DTT 铺平了道路。
