Catalytic thiolysis of chemoenzymatically derived vinylepoxides. Efficient synthesis of homochiral phenylthioconduritol F

The chemoenzymatic synthesis of enantiomerically pure phenylthioconduritol F obtained in 44% overall yield is described. The key step of the synthesis is the Yb(III) thiolysis of a vinyl epoxide, which was studied in depth. The methodology is amenable to scale up and expandable to the preparation of other thiocyclitols.