Synthesis of sporiolide B from D-glucal.
A total synthesis of the 12-membered ring natural macrolide, sporiolide B, was achieved from D-glucal in 17 steps with 4.8% overall yield. The required stereochemical configuration at C-3 and C-5 in sporiolide B was easily introduced by applying a Mitsunobu reaction on the chiral template D-glucal. Yamaguchi esterification and ring closing metathesis greatly improved the access to the target compound.
Chen
Qi
Q
State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, PR China.
Du
Yuguo
Y
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000737:chemistry; D006131:Growth Inhibitors / Q000737:chemistry; D006367:HeLa Cells; D006801:Humans; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D000461:Rhodophyta / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D006131:Growth Inhibitors; D007783:Lactones; D018942:Macrolides; C001289:d-glucal; D003847:Deoxyglucose