71593-69-6

Upstream product

• 71593-59-4 [2-Ethoxy-2-(3-methyl-cyclohex-2-enyloxy)-ethylselanyl]-benzene 
• 21378-21-2 3-methylcyclohex-2-en-1-ol 
• 78-39-7 Triethyl orthoacetate 

Downstream Products

• 63714-74-9 3-(1-Methyl-cyclohex-2-enyl)-propionic acid methyl ester 
• 147122-82-5 2-(1-methyl-2-cyclohexen-1-yl)acetyl chloride 
• 147591-30-8 1-Diazo-3-(1-methyl-cyclohex-2-enyl)-propan-2-one 
• 845877-20-5 6-methyltricyclo[4.3.0.0^2,9]nonan-8-ol 
• 368875-06-3 cis-9-Methyl-hydrindan-1-on 
• 147397-85-1 1-methyl-2-hydroxy-3-phenylselenenylcyclohexan-1-acetic acid lactone 
• 147397-85-1 (3aR,7aS)-3a-Methyl-7-phenylselanyl-hexahydro-benzofuran-2-one 

Relevant academic research and scientific papers

Synthetic studies towards daphniyunnine B: Construction of AC bicyclic skeleton with two vicinal all carbon quaternary stereocenters

The AC bicyclic skeleton of daphniyunnine B with the required 3 stereocenters (C4, C5 and C8) was accomplished in a concise route which featured two Claisen-type rearrangement reactions to construct the required vicinal all carbon quaternary stereocenters

Lithium-liquid ammonia mediated carbocyclisation of δ,ε- unsaturated esters: Annulation of cyclopentanones

Lithium-liquid ammonia mediated carbanion cyclisation of δ,ε-unsaturated esters leading to cyclopentanes, fused as well as spiro, via annulation is described.

Unexpected formation of bicyclo[3,3.1]nonenyl methanesulfonate from tricyclo[4.3.0.02,9]nonan-8-ol

Attempted methanesulfonylation reaction of the tricyclo[4.3.0.0 2,9]nonan-8-ol 8 under standard conditions led to the selective cleavage of the C1-C9 cyclopropane bond resulting in the formation of bicyclo[3.3.1]non-2-en-9

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.