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

• Main Authors: Vedachalam, Seenuvasan, Murugesh, Nithya, Chakraborty, Priyanka, Karvembu, Ramasamy, Liu, Xue-Wei
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2020
• Subjects: Science::Chemistry; Coates-Claisen; Oleuropein
• Online Access: https://hdl.handle.net/10356/142696
• Institution: Nanyang Technological University

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.