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.

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