Synthesis of two osteoclast-forming suppressors, demethylincisterol A3 and chaxine A

The synthesis of two potent osteoclast-forming suppressing agents isolated from the Chinese mushroom Agrocybe chaxingu, demethylincisterol A3 and chaxine A, was accomplished using ergocalciferol as the starting material. Our methodology for the synthesis of demethylincisterol A3 and chaxine A featured the construction of a butenolide moiety by the intramolecular Horner-Wadsworth-Emmons reaction under Masamune-Roush conditions. This is the first reported synthesis of chaxine A.