337919-17-2

Upstream product

• 74213-12-0 (E)-5-<(tert-butyldimethylsilyl)oxy>-1,3-pentadiene 

Downstream Products

• 337919-21-8 N-(8-hydroxymethyl-4-methoxy-5,8-dihydro-naphthalen-1-yl)-benzamide 
• 337919-23-0 N-[8-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-5,6,7,8-tetrahydro-naphthalen-1-yl]-benzamide 
• 337919-18-3 N-(8-hydroxymethyl-4-methoxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-benzamide 
• 337919-19-4 N-(8-formyl-4-methoxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-benzamide 

Relevant academic research and scientific papers

The Diels-Alder reactions of quinone imine ketals: A synthesis of the ergot skeleton

The high pressure (13 kbar) Diels-Alder reaction of N-benzoyl-p-benzoquinone-mono-imine dimethyl ketal with an appropriate diene yields, after treatment with anhydrous acid, a dihydronaphthanilide. Conversion to the tricyclic skeleton of the ergot alkaloids is effected via a series of simple transformations.