Pd-catalyzed Regio- and Stereoselective Hydrostannylation of an Alkyl Ethynyl Ether/One-Pot Stille Coupling Enables the Synthesis of 14-Membered Macrolactone of Luminamicin

Regio- and stereoselective hydrostannylation of alkyl ethynyl ethers generates alkenyl ethers, which are useful building blocks in organic synthesis. This efficient synthetic method, however, is limited. Here, we report not only an efficient method for a highly regio- and stereoselective Pd-catalyzed hydrostannylation of alkyl ethynyl ethers but also a scalable synthesis and construction of the core framework of luminamicin possessing all functional groups and stereocenters.

Automated summary

A highly efficient Pd-catalyzed hydrostannylation method for alkyl ethynyl ethers has been developed, allowing for the generation of alkenyl ethers with high regio- and stereoselectivity. This method also enables scalable synthesis and construction of the core framework of luminamicin, containing all functional groups and stereocenters.