01. Synthesis of a Meso Diol

This is a good introductory level synthesis that involves the use of a few reactions students typically learn in the first semester organic chemistry.

The key points here are to recognize that the meso diol can look differently if you rotate it around the middle C-C bond. This is a very common trick that many instructors use. At the end of the day, remember: molecules don’t care how you draw them!

This synthesis also makes a use of the dihydroxylation with osmium oxide reaction and the reduction of alkynes over Lindlar’s catalyst.