107953-24-2

Upstream product

• 107953-23-1 2-Phenylselanyl-3-((1S,5R)-2,5,6,6-tetramethyl-cyclohex-2-enyl)-propionitrile 
• 138703-08-9 6-Benzyloxy-3-methyl-1,3-hexadiene 
• 107953-12-8 (3aR*,7S*,7aS*)-7-(2-Benzyloxy)ethyl-6-methyl-3a,4,7,7a-tetrahydrophthalide 
• 107953-13-9 (3aR*,7S*,7aS*)-7-(2-Benzyloxy)ethyl-6,7a-dimethyl-3a,4,7,7a-tetrahydrophthalide 
• 107953-10-6 (1R*,2S*,3R*)-3-(2-Benzyloxy)ethyl-4-methyl-1,2,3,6-tetrahydrophthalic anhydride 
• 107953-11-7 (1R,2S,4S,5S,8S)-8-(2-Benzyloxy-ethyl)-4-iodo-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-2-carboxylic acid 
• 107953-21-9 (4R,6R)-6-(2-Hydroxy)ethyl-1,4,5,5-tetramethylcyclohexene 
• 107953-22-0 (4R,6R)-1-(1,4,5,5-Tetramethyl-1-cyclohexen-6-yl)acetaldehyde 
• 107953-20-8 (4R,6R)-6-(2-Benzyloxy)ethyl-1,4,5,5-tetramethylcyclohexene 
• 107953-18-4 (4S,6R)-6-(2-Benzyloxy)ethyl-4-hydroxymethyl-1,5,5-trimethylcyclohexene 
• 107953-15-1 (3aR,7S,7aS)-7-(2-Benzyloxy-ethyl)-6,7a-dimethyl-1,3,3a,4,7,7a-hexahydro-isobenzofuran-1-ol 
• 107953-15-1 (3aR*,7S*,7aS*)-7-(2-Benzyloxy)ethyl-6,7a-dimethyl-1-hydroxy-3a,4,7,7a-tetrahydro-(1,3H)-isobenzofuran 
• 107953-19-5 (4S,6R)-6-(2-Benzyloxy)ethyl-4-methanesulfonyloxymethyl-1,5,5-trimethylcyclohexene 
• 107953-17-3 (1R,3aS,7R,7aR)-7-(2-Benzyloxy)ethyl-6,7a-dimethyl-1-l-menthoxy-3a,4,7,7a-tetrahydro-(1,3H)-isobenzofuran 

Downstream Products

• 35124-13-1 (+)-(2R:6S)-cis-α-irone 
• 108033-18-7 (+)-(Z)-cis-α-Irone 

Relevant academic research and scientific papers

Synthesis of (+)- and (-)-cis-α-irones

A stereocontrolled total synthesis of natural (+)-cis-α-irone (1) is described. The key intermediate (+)-hemiacetal 15 was prepared from the diene 10 in six steps. The crucial optical resolution of (+)-15 was achieved by initial stereoselective conversion into the corresponding l-menthyl acetals 16 and 17 followed by separation and hydrolysis. One of the optically pure enantiomers of 15 was transformed to (-)-18 and then to (+)-1 in seven steps. The synthetic (+)-1 was found to be identical with the natural (+)-cis-α-irone. The isomeric (-)-cis-α-irone was also synthesized from the other enantiomer of 15, via (+)-18.