202258-27-3

Upstream product

• 202258-26-2 3-Isopropyl-4-methoxy-7-(5-oxo-pentyl)-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile 
• 202258-25-1 7-Hex-5-enyl-3-isopropyl-4-methoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile 
• 202258-28-4 7-(5-Hydroxy-pentyl)-3-isopropyl-4-methoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile 
• 128291-69-0 3-Isopropyl-4-methoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile 
• 18922-04-8 6-iodohex-1-ene 
• 873-55-2 sodium benzenesulfonate 
• 202258-29-5 7-(5-Bromo-pentyl)-3-isopropyl-4-methoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile 

Downstream Products

• 202258-20-6 [1-Benzenesulfonyl-5-(7-cyano-3-isopropyl-4-methoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-pentyl]-phosphonic acid diethyl ester 
• 202258-30-8 4-Isopropyl-5-methoxy-1-(5-phenylsulfonylhex-5-enyl)-1,2-dihydrobenzocyclobutene-1-carbonitrile 

Relevant academic research and scientific papers

Control of stereochemistry in an intramolecular Diels-Alder reaction by the phenylsulfonyl group; an improved synthesis of pisiferol

Thermolysis of 4a (X = H) gives 6a and 6b (X = H) in a ratio of 1:4 whereas 4b (X = SO2Ph) gives more of the trans-ring junction product 6a (X = SO2Ph) suitable for the synthesis of pisiferol [ratio 6a:6b (X = SO2Ph) = 1.5:1]. Base catalysed elimination of the phenylsulfonyl group from 6a (X = SO2Ph) gives 18 which is hydrogenated to 6a (X = H), an intermediate in the synthesis of pisiferol. Both 6a and 6b (X = SO2Ph) have ring B in a half-boat conformation.