177532-97-7

Upstream product

• 177532-96-6 (1R,2S,6R,9R)-9-isopropyl-1,2,6-trimethyl-3-oxabicyclo[4.4.0]decan-4-one 

Downstream Products

• 261957-26-0 (1S)-1-[(1R,2R,5R)-2-(tert-butyldimethylsilyloxyethyl)-5-isopropyl-1,2-dimethylcyclohexyl]ethanol 
• 5090-54-0 valeranone 
• 261957-25-9 2-[(1R,2R,4R)-2-acetyl-4-isopropyl-1,2-dimethylcyclohexyl]acetaldehyde 
• 261957-27-1 1-[(1R,2R,5R)-2-(2-tert-butyldimethylsilyloxyethyl)-5-isopropyl-1,2-dimethylcyclohexyl]-1-ethanone 

Relevant academic research and scientific papers

Enantiospecific total syntheses of (-)-valeranone

Two convenient methodologies have been described for the enantiospecific synthesis of (-)-valeranone 1. The hydrindanone 12, obtained from the readily and abundantly available monoterpene (R)-carvone, has been converted into the ketoaldehyde 16 via the alkene 15b. In another direction the lactone 18, obtained from the hydrindanone 12, has been elaborated into the ketoaldehyde 16 employing two methodologies. Intramolecular aldol condensation followed by hydrogenation transformed the ketoaldehyde 16 into (-)-valeranone 1.

Two regiospecific alternative strategies in the synthesis of (-)- valeranone

Two regiospecific modifications have been developed in the synthesis of valeranone. The first one is based on the regiospecific protection of a diol and the second is based on the Wittig reaction of a hemiacetal.

Stereo- and enantiospecific total synthesis of (-)-valeranone

Stereo- and enantiospecific total synthesis of the irregular sesquiterpene, valeranone, starting from S-6-methylcarvone employing a hydrindanone to decalone ring expansion methodology, is described.