Flow Pd(II)-Catalysed Carbonylative Cyclisation in the Total Synthesis of Jaspine B

Abstract

This work describes the total synthesis of jaspine B involving the highly diastereoselective Pd(II)-catalysed carbonylative cyclisation in the preparation of crucial intermediates. New conditions for this transformation were developed and involved the pBQ/LiCl as a reoxidation system and Fe(CO)5 as an in situ source of stoichiometric amount of carbon monoxide (1.5 molar equivalent). In addition, we have demonstrated the use of a flow reactor adopting proposed conditions in the large-scale preparation of key lactones.

Keywords

• Jaspine B
• flow chemistry
• palladium catalysis
• cyclisation
• carbonylation