Piperovatine synthesis

[AJR]

Hi,

 

I'm a scientist in LA and want to do an experiment with Piperovatine:

 

(2E4E) n Isobutyl -6-(4-methoxyphenol)hexa-2,4-dienamide

 

Does anyone know a synthetic organic chemist who I could pay to make it for me? I'm in Los angeles and I would be grateful for any help...

 

Sincerely,

 

AJR

216-832-7905

piperovatine.pdf

[UC]

I'm not sure where to dig up someone who can make it for you, but I have attached a reasonable synthesis strategy. Compounds (1) and (2) at the bottom may also be of interest. (1) is a semisynthetic derivative of commercially available piperine, substituting in isobutylamine for the piperidine that normally constitutes the amide. (2) is the (2Z,4Z) isomer of your target compound, and easily produced by use of lindlar's catalyst for catalytic hydrogenation instead of a birch reduction.