Proposed Synthesis of Compound C:

 

Jason Grimm

Adam Book

Rob Hillard

 

 

 

 

 

 

Our proposed synthesis of Compound E begins as such: begin the reaction by introducing a bromo-ethane to alkyl-3-ol (Bruice 255).  Using pyridine as a solvent, add tosyl chloride (TsCl) to your alcohol (Bruice 436).  The tosylate ion (^-OTs) is an excellent leaving group.  Preparing an organometallic bromo-propane will allow substitution between tosylate ion itself and the tosylate group (Bruice 434).  From there, a reaction of our compound with one equivalent of sodium in liquid ammonia will produce our desired trans alkene (Bruice 251).