130255-06-0

Upstream product

• 130255-05-9 7-ethyl-3,4-dihydro-2H-1-benzopyran-2-one 
• 152033-69-7 7-ethylcoumarin 
• 620-17-7 3-ethylphenol 
• 152033-70-0 7-ethyl-2-chromanol 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 152033-72-2 (E)-5-(1-Acetoxy-4-ethyl-6-oxo-cyclohexa-2,4-dienyl)-pent-2-enoic acid ethyl ester 
• 130274-13-4 (3aR,5R,6S,7aR)-6-Ethyl-1-oxo-octahydro-indene-4,5-dicarboxylic acid 4-ethyl ester 
• 62251-98-3 (+/-)-(3a,6-trans; 3a,7a-cis)-6-ethyl-4-(hydroxymethyl)-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carboxylate 

Relevant academic research and scientific papers

The Synthesis of (+/-)-Coronafacic Acid by a Tandem Wessely Oxidation-Diels-Alder Reaction Sequence

(+/-)-Coronafacic acid (9) has been synthesized from ethyl 5-(4-ethyl-2-hydroxyphenyl)pent-2-enoate (4) via a tandem Wessely oxidation-Diels-Alder reaction sequence.

Tandem Wessely oxidation and intramolecular Diels-Alder reactions. IV. The synthesis of (+/-)-coronafacic acid

Ethyl E-5-(4-ethyl-2-hydroxyphenyl)-2-pentenoate (7), prepared in four steps from m-ethylphenol (9), was converted via Wessely oxidation with lead tetraacetate followed by intramolecular Diels-Alder reaction in boiling xylene to ethyl 1-acetyloxy-6-ethyl-2,3,3a,4,5,7a-hexahydro-8-oxo-1,5-methano-1H-indene-anti-4-carboxylate (16).Hydrogenation of 16 followed by mild hydrolysis gave ethyl 6-ethyloctahydro-1-hydroxy-8-oxo-1,5-methano-1H-indene-anti-4-carboxylate (24), which on oxidation with periodate gave 4-(ethoxycarbonyl)-6-ethyloctahydro-1-oxo-1H-indene-5-carboxylic acid (26).Oxidative decarboxylation of this gave a mixture of ethyl 6-ethyl-2,3,3a,6,7,7a-hexahydro-1-oxo-1H-indene-4-carboxylate (31) and ethyl 6-ethyl-2,3,3a,4,7,7a-hexahydro-1-oxo-1H-indene-4-carboxylate (32); the latter was converted to the former by ethanolic sodium ethoxide.Hydrolysis of 31 with hot hydrochloric acid gave (+/-)-coronafacic acid (4).