144654-01-3

Upstream product

• 144653-99-6 2-Methyl-4-(2',2',6'-trimethylcyclohex-1'-enyl)-2-trimethylsilyloxybutyronitrile 
• 17283-81-7 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on 

Downstream Products

• 144654-04-6 2-<4',5'-Dihydroxy-5'-methyl-7'-(2'',2'',6''-trimethylcyclohex-1''-enyl)heptanoyl>-1-methoxymethylimidazole 
• 144654-02-4 2-<4'-Hydroxy-5'-methyl-1'-triisopropylsilyloxy-7'-(2'',2'',6''-trimethylcyclohex-1''-enyl)-5'-trimethylsilyloxyhept-1'-enyl>-1-methoxymethylimidazole 
• 84316-05-2 (+/-)-Cavernosine 
• 84316-05-2 (+/-)-Epicavernosine 

Relevant academic research and scientific papers

Synthesis of γ-Lactones from intermediate 2-(γ-Hydroxyacyl)imidazoles by N-Methylation and Base-catalyzed C-C Bond Cleavage. Application to the Synthesis of (+/-)-Cavernosin

Reaction of the allyl anions of O-trialkylsilyl-N-alkyl-2-(1'-hydroxyprop-2'-enyl)imidazoles with aldehydes and ketones gives products of α- and γ-attack.Greater steric hindrance in the anion (triisopropyl vs t-butyldimethylsilyl) and in the aldehyde or ketone favours the γ-products.Sequential desilylation, N-methylation and treatment with base resulted in cleavage of these products to γ-lactones.The method was applied to the synthesis of (+/-)-cavernosine.