140386-30-7

Upstream product

• 13720-12-2 4-(2',2'-Dimethyl-6'-methylidenecyclohexyl)butan-2-one 
• 3796-70-1 trans geranyl acetone 
• 41641-14-9 1-hydroxymethyl-3,3-dimethyl-cyclohex-1-ene 
• 61188-00-9 (Z)-6-(hydroxymethylene)-2,2-dimethylcyclohexanone 
• 583-60-8 2-Methylcyclohexanone 
• 1193-18-6 3-methylcyclohexen-2-one 
• 77239-52-2 dihydro-γ-ionone ethylene acetal 
• 3879-26-3 (Z)-nerylacetone 
• 77239-50-0 3,3-dimethyl-2-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclohexanone 
• 61175-92-6 3,3-dimethyl-1-<(trimethylsilyl)oxy>cyclohex-1-ene 
• 89307-60-8 Ethyl 4-(2-methylene-6,6-dimethylcyclohexyl)-2-methyl-2,3-epoxybutyrate 
• 76337-18-3 3,3-Dimethylcyclohex-1-ene-1-carbaldehyde 
• 547-15-9 2-(6',6'-Dimethyl-2'-methylenecyclohexyl)ethanal 
• 76337-19-4 (3,3-Dimethylcyclohexenyl)methyl vinyl ether 

Relevant academic research and scientific papers

Stereoselective Directed Cationic Cascades Enabled by Molecular Anchoring in Terpene Cyclases

Cascade reactions appeared as a cutting-edge strategy to streamline the assembly of complex structural scaffolds from naturally available precursors in an atom-, as well as time, labor- and cost-efficient way. We herein report a strategy to control cation

Titanium-catalyzed enantioselective synthesis of α-ambrinol

We describe the first enantioselective synthesis of the odorant compound (-)-α-ambrinol (96% ee) from commercial geranylacetone. The key steps are a Jacobsen's asymmetric epoxidation and a titanium-catalyzed stereoselective cyclization initiated by radical epoxide opening. The oxirane ring opening proceeds with retention of configuration at the epoxide chiral center, giving a secondary alcohol which can be advantageously exploited to raise the ee provided by the synthetic sequence. We also synthesized (+)-α-ambrinol by a closely related procedure, showing the synthetic versatility of combining titanium-catalyzed cyclization with Jacobsen's epoxidation reactions.

Biomimetic cyclization of small terpenoids promoted by zeolite NaY: Tandem formation of α-ambrinol from geranyl acetone

Zeolite NaY promotes efficiently the biomimetic cyclization of small acyclic terpenes. Geranyl and neryl acetone undergo a novel tandem 1,5-diene cyclization/carbonyl-ene reaction to form the natural product α-ambrinol isolated in >65% yield.

New Synthesis of γ-Homocyclogeranial, γ-Dihydroionone and Their Derivatives

A new and efficient synthesis of γ-homocyclogeranial (4), γ-dihydroionone (3) and their derivatives, 5, 6, 7 and 8, volatile components of ambergris, is described.Their compounds were synthesized via Claisen rearrangement of (3,3-dimethylcyclohexenyl)methyl vinyl ether (14).

SYNTHESIS OF (+/-)-α-AMBRINOL

Synthesis of α-ambrinol was successfully accomplished by cyclization of dihydro-γ-ionone ethylene acetal which was prepared by the titanium(IV)-promoted reaction of 3,3-dimethyl-1-trimethylsiloxycyclohexene with methyl vinyl ketone ethylene acetal followed by exomethylenation with triphenylphosphonium methylide.