# Synthesis of (1S,2S,4S)-4-ethenyl-5-methylcyclohexane-1,2-diol

I'm trying to devise a synthesis for the following question.

I am aware it involves retrosynthetic, Wittig, Grignard and diels alder reactions, but unfortunately I can't really grasp all concepts which make me stuck. If there's any help or further explanation would be great.

I have tried to do retrosynthetic for the alkyne compound, also the Wittig reaction. I think Grignard should be the last step where it will change the oxygen bond to $$\ce{OH}$$. But I can't get myself to there yet.

• I would start with the commercially available methyl propiolate and do the D-A on that first May 21 at 7:16