25090-79-3

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 931, 1984 DOI: 10.1021/jo00179a036Tetrahedron Letters, 35, p. 6075, 1994 DOI: 10.1016/0040-4039(94)88079-4

Upstream product

• 29784-44-9 5-Chloro-2,3-dimethyl-3-p-tolyl-hex-5-en-2-ol 
• 75-11-6 diiodomethane 
• 58812-72-9 4,4-dimethyl-3-(4-methylphenyl)-cyclopent-2-en-1-one 
• 106-38-7 para-bromotoluene 
• 30434-65-2 3,4,4-trimethylcyclopent-2-en-1-one 
• 85090-95-5 4,5,5-Trimethyl-4-p-tolyl-1-oxa-spiro[2.3]hexane 
• 75-24-1 trimethylaluminum 
• 58812-74-1 4,4-Dimethyl-5-p-tolyl-bicyclo[3.1.0]hexan-2-one 
• 51116-82-6 2-Cyan-3.3-dimethyl-4-p-tolylvaleriansaeure 
• 51116-86-0 (1.1-Dimethyl-2-p-tolylpropyl)malonsaeure 
• 1021150-67-3 2-methyl-5-(1,5,5-trimethyl-3-oxocyclopentyl)bicyclo[3.1.0]hexan-2-ol 
• 109334-10-3 (4R)-3,4-dimethyl-4-(p-tolyl)-2-cyclopentenone 
• 515826-81-0 MeCu*BF₃ 
• 124909-15-5 (R)-3,3,4-Trimethyl-4-p-tolyl-hexanedioic acid 

Relevant academic research and scientific papers

Total synthesis of (±)-β-microbiotene, (±)-microbiotol, (±)-cyclocuparanol and (±)-β-cuparenones

Total synthesis of (±)-β-microbiotene, (±)-microbiotol, (±)-cyclocuparanol and their epimers along with (±)-β- cuparenone has been described. A combination of orthoester Claisen rearrangement, an acid catalysed rearrangement of a diazoketone for the gener

A short and efficient synthesis of (±)-β-cuparenone

A Wittig olefination-Claisen rearrangement strategy has been applied to achieve one of the shortest and efficient synthesis of (±)-β-cuparenone.

Nickel-catalysed conjugate addition to trimethylaluminum to sterically hindered α,β-unsaturated ketones

Nickel acetylacetonate is an efficient catalyst for the 1,4-addition of trimethylaluminum to α,β-unsaturated ketones. The reaction is strongly solvent dependent and gives best results in tetrahydrofuran or ethyl acetate. The reaction is especially useful for the nucleophilic 1,4-methyl transfer to sterically hindered enones. A β-cuparenone synthesis via conjugate methyl group addition to an enone precursor is described.

Total Synthesis of (+/-)-Cyclolaurene, (+/-)-Epicyclolaurene and (+/-)-β-Cuparenone

The first total synthesis of (+/-)-cyclolaurene (1) and (+/-)-epicyclolaurene (5), and a new route to (+/-)-β-cuparenone (4) are reported.Thus, orthoester Claisen rearrangement of the cinnamyl alcohol 8 furnished the ene-ester 10.Anhydrous CuSO4 catalysed

ENANTIOCONTROLLED SYNTHESES OF THE CUPARENE SESQUITERPENES, (-)-HERBERTENE, (+)-β-CUPARENONE, (-)-DEBROMOAPLYSIN, AND (-)-APLYSIN

Enantiocontrolled syntheses of the Cuparene sesquiterpenes, (-)-herbertene, (+)-cuparenone, (-)-debromoaplysin, and (-)-aplysin, have been achieved starting from the optically active tricyclic dienone by employing a Fischer indolization reaction under non-acidic conditions as the key step.

SYNTHESIS AND UTILIZATION OF OPTICALLY ACTIVE 2-SUBSTITUTED 4-(TRIMETHYLSILYL)CYCLOPENTANONES: SYNTHESIS OF (-)-MASSOIALACTONE AND (+)-β-CUPARENONE

Ring contraction by BF3*Et2O catalyzed epoxide rearrangement of 3-substituted 5-trimethylsilyl-2,3-epoxycyclohexanones gave the corresponding 2-substituted 4-(trimethylsilyl)cyclopentanones diastereoselectively.Synthesis of (-)-massoialactone and (+)-β-cuparenone utilizing the above transformation is also described.

TOTAL SYNTHESIS OF (R)-(-)-β-CUPARENONE

(R)-(-)-β-Cuparenone has been synthesized from (S)-(+)-acid-2 obtained via resolution of the racemic acid.Two of the noteworthy steps are (a) repeated methylation of ester (+)-8 with LDA/MeI to furnish (+)-10 and (b) the reaction of 12, having two neopent

Ultrasound in Organic Synthesis. 7. Preparation of Organozinc Reagents and Their Nickel-Catalyzed Reactions with α,β-Unsaturated Carbonyl Compounds

Diorganozinc compounds can be prepared with great ease and efficiency in a one-pot process, by sonication of lithium, an organic halide, and a zinc halide in THF or toluene mixtures.The reagents thus obtained give rise to clean and selective conjugate additions to α,β-unsaturated aldehydes and ketones in the presence of catalytic amounts of nickel acetylacetonate.