225221-32-9

Upstream product

• 64243-08-9 (+)-(1R,5R)-2⁽¹⁰⁾-Pinen-4-on 
• 557-34-6 zinc diacetate 
• 225221-30-7 (R)-(-)-1-acetoxy-4-(1-acetoxy-1-methylethyl)-5-(methylene)cyclohexene 

Downstream Products

• 116724-19-7 (S)-(-)-4-isopropyl-3-methyl-2-cyclohexen-1-one 
• 89064-06-2 (S)-(+)-4-isopropenyl-3-methyl-2-cyclohexen-1-one 

Relevant academic research and scientific papers

BF3-induced cyclobutane-opening of verbenone and its deconjugate homolog. Efficient preparation of o-mentha-1,8-dien-3-one and o-menth-1-en- 3-one in optically active forms

Starting with (+)-verbenone, readily obtainable from (+)-nopinone, enantioselective preparation of (S)-(+)-4-isopropenyl-, (S)-(-)-4-isopropyl- and (R)-(+)-4-(1-acetoxy-1-methylethyl)-3-methyl-2-cyclohexen-1-ones was accomplished with little loss of stereochemical integrity via BF3-induced cyclobutane-opening of (+)4-(methylene)nopinone. As we have developed an efficient chemical transformation of (+)-nopinone into (-)-verbenone, the present syntheses of the above cyclohexenones are formal syntheses of their enantiomers from (+)-nopinone.