1141-54-4

Upstream product

• 622-47-9 4-tolylacetic acid 
• 23430-44-6 (S)-2-(4-methylphenyl)-1-propyl p-toluenesulfonate 
• 93922-51-1 (S)-2-(4-methylphenyl)-1-propanol 
• 39724-80-6 ar-E-Atlantone 
• 122-00-9 para-methylacetophenone 
• 113283-35-5 2-Hydroxy-2-(p-tolyl)-6-methylhept-5-en-4-one 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 93922-52-2 (R)-3-(4-methylphenyl)butanoic acid 
• 848674-80-6 (4S,2'S)-4-benzyl-3-[(4-methylphenyl)-2-propanoyl]-2-oxazolidinone 
• 848674-79-3 (S)-4-benzyl-3-(4-methylphenylacetyl)-2-oxazolidinone 
• 3017-69-4 2-methyl-1-propenylbromide 
• 848674-84-0 (R)-N-methyl-N-methoxy-3-(4-methylphenyl)butanamide 
• 765916-52-7 (6R)-2-methyl-6-(p-tolyl)hept-2-en-4-ol 

Downstream Products

• 70855-59-3 (+)-(1S,3R)-mutisianthol 

Relevant academic research and scientific papers

Lewis Base-Catalyzed Enantioselective Conjugate Reduction of β,β-Disubstituted α,β-Unsaturated Ketones with Trichlorosilane: E/ Z-Isomerization, Regioselectivity, and Synthetic Applications

The chiral bisphosphine dioxide-catalyzed asymmetric conjugate reduction of acyclic β,β-disubstituted α,β-unsaturated ketones with trichlorosilane affords saturated ketones having a stereogenic carbon center at the carbonyl β-position with high enantioselectivities. Because the E/Z-isomerizations of enone substrates occur concomitantly, reduction products with the same absolute configurations are obtained from either (E)- or (Z)-enones. Conjugate reduction is accelerated in the presence of an electron-rich aryl group at the β-position of the enone owing to its carbocation-stabilizing ability. Computational studies were also conducted in order to elucidate the origin of the observed enantioselectivity. The regio- and enantioselective reductions of dienones were realized and applied to the syntheses of ar-turmerone, turmeronol A, mutisianthol, and jungianol, which are optically active sesquiterpenes.

Total synthesis of (R)- and (S)-turmerone and (7S,9R)-bisacumol by an efficient chemoenzymatic approach

An enantioselective synthesis of (R)-, (S)-turmerone and (7S,9R)-bisacumol is described. The enantiomerically pure key intermediates, a substituted butanoate ester and acid are utilized in the synthesis of both enantiomers of turmerone. The lipase catalyzed resolution studies of the acetate of bisacumol have been exploited towards the total synthesis of the naturally occurring cytotoxic sesquiterpene, (7S,9R)-bisacumol with high diastereoselectivity (94% de).

Organic synthesis in pheromone science

Examples are given to illustrate the use of chemical and/or enzymatic asymmetric reactions in the synthesis of the new pheromones of the broad-horned flour beetle, flea beetle, currant stem girdler and Colorado potato beetle. The relationships between ste

Synthesis of (R)-ar-turmerone and its conversion to (R)-ar-himachalene, a pheromone component of the flea beetle: (R)-ar-himachalene is dextrorotatory in hexane, while levorotatory in chloroform

(R)-ar-Turmerone was synthesized from (4-methylphenyl)acetic acid by employing Evans asymmetric alkylation as the key step. (R)-ar-Turmerone was converted to (R)-ar-himachalene, which was dextrorotatory in hexane while levorotatory in chloroform. Enantiomerically impure (75% ee) (R)-3-(4-methylphenyl)butanoic acid crystallized more readily than the enantiomerically pure one.

Chiral benzyl centers through asymmetric catalysis. A three-step synthesis of (R)-(-)-α-curcumene via asymmetric hydrovinylation

(Chemical Equation Presented) A three-step, two-pot procedure involving asymmetric hydrovinylation followed by Suzuki-Miyaura reaction represents by far the shortest synthesis of this popular bisabolane. Other applications for the synthesis of similar com

STEREOSTRUCTURE OF CURLONE, A SESQUITERPENOID OF CURCUMA LONGA RHIZOMES

From the crude drug 'ukon' (turmeric) (obtained from the rhizomes of Curcuma longa) a new sesquiterpenoid, curlone, has been isolated and shown as (6S)-2-methyl-6--2-hepten-4-one on the basis of its spectral properties