A short total synthesis of (+)-furanomycin.
[reaction: see text] 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 alpha-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.
VanBrunt
M P
MP
Texas A&M University, Department of Chemistry, College Station 77842-3012, USA.
Standaert
R F
RF
D000596:Amino Acids / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D013302:Streptomyces / Q000737:chemistry
D000596:Amino Acids; C063753:furanomycin