147397-89-5

Upstream product

• 18383-51-2 (-)-trans-carveol 
• 78-39-7 Triethyl orthoacetate 
• 99-48-9 R-(+)-carveol 
• 6485-40-1 (R)-Carvone 
• 99-48-9 (4R,6R)-carveol 
• 167611-58-7 (1R,5R)-ethyl <(2-methyl-5-isopropenyl)-cyclohex-2-ene>-1-acetate 
• 99-48-9 5-Isopropenyl-2-methyl-cyclohex-2-enol 
• 140137-55-9 (5-Isopropenyl-2-methyl-cyclohex-2-enyl)-acetic acid ethyl ester 

Downstream Products

• 744208-15-9 (1S,5S,7R,8S,9S)-8,9-dimethyl-3-oxo-2-oxatricyclo[5.2.1.0^5,9]decan-8-ol 
• 744208-15-9 (1S,5S,7R,8R,9S)-8,9-dimethyl-3-oxo-2-oxatricyclo[5.2.1.0^5,9]decan-8-ol 
• 744207-92-9 (1R,2S,4R,6S)-[4-hydroxy-1-methyl-7-oxabicyclo[4.1.0]hept-2-yl]acetic acid methyl ester 
• 175695-67-7 1-Diazo-3-((1R,5S)-5-isopropenyl-2-methyl-cyclohex-2-enyl)-propan-2-one 

Relevant academic research and scientific papers

Cp2TiCl-promoted isomerization of trisubstituted epoxides to exo-methylene allylic alcohols on carvone derivatives

The ring-opening reaction of trisubstituted epoxides promoted by Cp 2TiCl led to exo-methylene allylic alcohols as major compounds when 0.5 M solutions of the epoxides were added to 0.1 M solutions of the reagent at room temperature in THF. In most cases, the allylic alcohols were contaminated with saturated alcohols. Normal and reverse addition modes led to the alternate product being favored. The different stereochemical outcome of cis- and trans-epoxy acetates is rationalized in terms of mechanistically biased elimination processes.

Novel stereocontrolled synthesis of the tricyclic lactone (1R,3R, 6R,9S)-6,9-dimethyl-8-oxo-7-oxatricyclo[4.3.0.03,9]nonane

The stereocontrolled synthesis of (1R,3R,6R,9S)-6,9-dimethyl-8-oxo-7-oxatricyclo[4.3.0.03,9]nonane 1 from (R)-(-)-carvone has been accomplished by application of a 13-step sequence with 12% overall yield. The absolute stereochemistry of the uns

Enantioselective synthesis of both (+)-and (-)-derivatives of bicyclo[4.3.0]nonan-8-one and -3,8-diones from R-carvone 1

Enantioselective synthesis of both the enantiomeric forms of the hydrindane derivatives mentioned in the title, potential chiral precursors in terpenoid synthesis, starting from R-carvone employing two different cyclopentannulation methodologies is described.

The claisen rearrangement in synthesis: Acceleration of the johnson orthoester protocol en route to bicyclic lactones

Catalysis of the Claisen orthoester rearrangement of triethyl orthoacetate and a number of 2-cycloalken-1-ols has been achieved using acidic catalysis and brief microwave thermolysis in DMF. Unlike conventional methods of thermolysis, very high yields of rearranged products are typically obtained in less than ten minutes, and the Claisen products themselves require no further purification. The synthetic utility of the products so obtained is demonstrated in a general synthesis of functionalized bicyclic lactones.