ol005569j_si_007.pdf (100.28 kB)

A Short Total Synthesis of (+)-Furanomycin

Download (100.28 kB)
journal contribution
posted on 09.02.2000, 00:00 by Michael Pete VanBrunt, Robert F. Standaert
Furanomycin is a Streptomyces metabolite that substitutes for isoleucine in protein translation. We report a concise and modular synthesis starting from the Garner aldehyde and proceeding in seven steps to furanomycin. The key steps include a stereoselective acetylide addition and the Ag+-mediated cyclization of an α-allenic alcohol to construct the trans-2,5-dihydrofuran. The efficiency (12% overall yield) and flexibility of the route will provide ample quantities of furanomycin and analogues for protein engineering.