Proposed Synthesis of Compound B

Bryan Cole

 

 

 

1.      Start with a 3-carbon long, terminal alkyne.  The NaNH­­­­­­₂ removes a proton, allowing the alkyl bromide to react, forming a 5-carbon long alkyne.

2.      Adding one equivalent of HBr will form both 2-bromopentane and 3-bromopentane.  Separation of the two products will be necessary.

3.      The addition of the next C-C bond is done by substituting the bromine with an ethyl group.

4.      Finally, the double bond is hydrogenated using hydrogen and paladium over carbon.