An Efficient Synthesis of a Cyclic Ether Key Intermediate for 9-Membered Masked Enediyne Using an Automated Synthesizer

Naturally occurring antibiotics containing 9-membered enediynes have received considerable attention for many years due to their potent DNA-cleaving activity. We previously reported the design and synthesis of a synthetic, masked 9-membered enediyne that possesses DNA-cleaving activity. Despite the importance of the 9-membered enediynes, application of these molecules is limited by their difficult synthesis. Herein, we report an improved process for the generation of a synthetic, masked 9-membered enediyne that uses an automated synthesizer for the production of a key synthetic intermediate.