58403-93-3

Upstream product

• 487-51-4 4-carbethoxy-3-methyl-2-cyclohexen-1-one 
• 174788-38-6 4-hydroxymethyl-3-methyl-2-cyclohexene-1-ol 

Downstream Products

• 117106-83-9 4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-cyclohex-2-enone 
• 174788-39-7 4-(tert-butyldimethylsilyloxy)methyl-3,3-dimethylcyclohexanone 
• 153864-92-7 2-diazo-3,3-dimethyl-4-tert-butyldimethylsilyloxymethylcyclohexanone 
• 174788-15-9 4-(tert-Butyl-dimethyl-silanyloxymethyl)-2-dimethoxymethyl-1,3,3-trimethyl-cyclohexanol 
• 174788-16-0 4-(tert-butyldimethylsilyloxy)methyl-3,3-dimethyl-1-trimethylsilyloxycyclohex-1-ene 

Relevant academic research and scientific papers

Abnormal Ito-Saegusa oxidation of TIPS enol ether assisted by a hydroxy group on a side chain

Although Ito-Saegusa oxidation gives defined α,β-unsaturated ketones from silyl enol ether of ketones controlled by the position of the sp2 carbon of the silyl enol ether, the formation of a regioisomeric product that was oxidized abnormally wa

A cycloaddition approach to tricyclic taxoid skeletons

A cycloaddition approach to the functionalized tricyclo[9.3.1.03,8]pentadecene skeleton contained in Taxol is described. The cyclohexenone 13 was converted as illustrated to the nitrile-aldehyde 24 to which the diene and acetylenic side chains were attached by sequential nucleophilic additions. Removal of the trimethylsilyl protecting group and Dess-Martin oxidation afforded the triene 35. Microwave-assisted thermal cyclization stereoselectively generated the tricyclic ketone 36 whose structure was further established by conversion to the aromatic system 37 upon treatment with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). An epoxidation sequence was developed to introduce the epimeric C13 alcohol 47 as required for this cycloaddition strategy. Alternatively, an allylic oxidation (CrO3, 3,5-dimethylpyrazole) afforded the C13 ketone 49.

Dihydrofurans from α-diazoketones: Facile rearrangement of donor-acceptor cyclopropanes

The direct synthesis of dihydrofurans 7, 11, and 23-25 from α-diazoketones 3, 8, and 20-22 is described. The cyclopropane intermediates generated upon treatment of the α-diazoketones with metal catalysts in the presence of ethyl vinyl ether rearranged spo

A NEW AND FACILE PERHYDROAZULENE FORMATION: THE TOTAL SYNTHESIS OF THE CAROTANE (+)-DAUCENE

Thermolysis of the 2,5-bis(trimethylsiloxy)tricyclo2,5>decan-7-ones 3 leads to perhydroazulenes by a transannular reaction involving an oxygen to oxygen migration of a silyl group in the intermediate cyclodecadienones.This 3-step transf