NHC catalyzed enantioselective Coates-Claisen rearrangement: a rapid access to the dihydropyran core for oleuropein based secoiridoids

作者：Vedachalam Seenuvasan^*; Murugesh Nithya; Chakraborty Priyanka; Karvembu Ramasamy; Liu Xue Wei^*

来源：New Journal of Chemistry, 2018, 42(3): 1832-1839.

DOI：10.1039/c7nj04057a

We present the short synthesis of the suitably functionalized enantioselective dihydropyran core of secoiridoids using an N-heterocyclic carbene (NHC) catalyzed Coates-Claisen rearrangement mechanism. The key steps of the synthesis are (i) the highly enantioselective NHC catalyzed Coates-Claisen rearrangement for the dihydropyran core, (ii) the assembly of the target dihydropyran core structure of oleuropein from a highly diastereoselective exocyclic trans alkene, and (iii) the highly stereoselective assembly of a monoterpene elenolide core structure.

• 出版日期2018-2-7
• 单位南阳理工学院