Organic Synthesis Laboratory, School of Basic Sciences, Indian Institute of Technology Bhubaneswar, Khurdha-752050, Odisha, India.
Org Biomol Chem. 2019 Jul 17;17(28):6831-6842. doi: 10.1039/c9ob00855a.
A simple and general approach towards the total syntheses of several iridolactones such as (±)-boschnialactone, (±)-7-epi-boschnialactone, (±)-teucriumlactone, (±)-iridomyrmecin, (±)-isoboonein, (±)-7-epi-argyol, (±)-scabrol A, (±)-7-epi-scabrol A, and (±)-patriscabrol as well as the putative structure of scholarein A is delineated. The synthetic strategy features a diastereoselective intramolecular Pauson-Khand reaction (IPKR) to construct the iridoid framework followed by some strategic synthetic manipulations to access the targeted monoterpenes including those having diverse oxy-functionalization patterns and with 3-5 contiguous stereogenic centres in a highly stereocontrolled manner. Also, the present endeavour includes the first total synthesis of scabrol A.
本文阐述了一种简单通用的方法，可用于合成多种环烯醚萜内酯，如（±）-boschnialactone、（±）-7-epi-boschnialactone、（±）-teucriumlactone、（±）-iridomyrmecin、（±）-isoboonein、（±）-7-epi-argyol、（±）-scabrol A、（±）-7-epi-scabrol A 和（±）-patriscabrol，以及 scholarein A 的假定结构。该合成策略的特点是采用非对映选择性分子内 Pauson-Khand 反应（IPKR）构建环烯醚萜骨架，然后进行一些策略性的合成操作，以高立体选择性的方式获得目标单萜，包括具有不同含氧官能团化模式和 3-5 个连续立体中心的单萜。此外，本研究还包括 scabrol A 的首次全合成。
