Synthesis of the proposed structure of tyroscherin, a growth inhibitor of IGF-1-dependent tumor cells, was succeeded. However, spectroscopic data of synthetic compound were not identical to those of natural tyroscherin. The stereochemistry of tyroscherin was revised to 2S,3R,8R,10R by synthesis of several stereoisomers. The first total synthesis of tyroscherin was achieved by using one-pot Julia coupling. Over all yield was 18.7% in thirteen steps from L-tyrosine. Synthetic tyroscherin exhibited the most selective and strongest activity among stereoisomers and synthetic analogs, against IGF-1-dependent tomor cells.
