84316-05-2

Upstream product

• 17283-81-7 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on 
• 115297-12-6 5-[1-Methyl-3-(2,6,6-trimethyl-cyclohex-1-enyl)-1-trimethylsilanyloxy-propyl]-5H-furan-2-one 
• 144654-01-3 2-Methyl-4-(2',2',6'-trimethylcyclohex-1'-enyl)-2-trimethylsilyloxybutyraldehyde 
• 144653-99-6 2-Methyl-4-(2',2',6'-trimethylcyclohex-1'-enyl)-2-trimethylsilyloxybutyronitrile 
• 144654-04-6 2-<4',5'-Dihydroxy-5'-methyl-7'-(2'',2'',6''-trimethylcyclohex-1''-enyl)heptanoyl>-1-methoxymethylimidazole 
• 115297-14-8 (R)-5-[(S)-1-Hydroxy-1-methyl-3-(2,6,6-trimethyl-cyclohex-1-enyl)-propyl]-5H-furan-2-one 
• 115297-14-8 (S)-5-[(S)-1-Hydroxy-1-methyl-3-(2,6,6-trimethyl-cyclohex-1-enyl)-propyl]-5H-furan-2-one 

Downstream Products

• 84316-08-5 C₂₂H₃₂⁽²⁾H₆O₄ 
• 84316-07-4 Acetic acid (4R,5S)-4,5-dihydroxy-5-methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-heptyl ester 
• 17283-81-7 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on 
• 84316-06-3 (4R,5S)-5-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-heptane-1,4,5-triol 

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.

THE SYNTHESIS OF (+/-)-CAVERNOSINE

The title compound and its epimer were synthesized in three and two steps from dihydro-β-ionone and 2-trimethylsiloxyfuran in 38 and 63percent overall yields respectively.Their relative configurations were confirmed by X-ray of an intermediate.