70287-32-0

Upstream product

• 38142-44-8 (R,E)-methyl 3-(4-methyl-3-cyclohexenyl)-2-butenoate 
• 73088-68-3 (1'R)-(2E)-3-methyl-3-(4'-methylcyclohexen-3'-yl)-propen-2-al-1 
• 5989-27-5 D-limonene 
• 6090-09-1 methyl-[(1R)-4-methylcyclohex-3-enyl]ketone 
• 77614-30-3 (R)-(+)-3-(4-methyl-3-cyclohexen-1-yl)-3-buten-1-ol 

Downstream Products

• 70286-27-0 (R)(E)-3-<4-Methyl-cyclohex-3-enyl>-but-2-enylbromid 
• 77647-36-0 (1'R)-(5E)-6-methyl-6-(4'-methylcyclohexen-3'-yl)hexen-5-one-2 
• 77647-38-2 methyl(1'R)-(2Z,6E)-3,7-dimethyl-7-(4'-methylcyclohexen-3'-yl)heptadien-2,6-oate 
• 77647-37-1 methyl (1'R)-(2E,6E)-3,7-dimethyl-7-(4'-methylcyclohexen-3'-yl)-heptadien-2,6-oate 
• 77647-40-6 methyl (1'R)-(2Z,6E)-3,7-dimethyl-7-(3'-bromo-4'-hydroxy-4'-methylcyclohexyl)-heptadien-2,6-oate 
• 77614-32-5 methyl (1'R)-(2E,6E)-3,7-dimethyl-7-(3'-bromo-4'-hydroxy-4'-methylcyclohexyl)-heptadien-2,6-oate 
• 138117-27-8 (S)-3-((S)-4-methylcyclohex-3-en-1-yl)butanal 

Relevant academic research and scientific papers

Multicatalytic approach to one-pot stereoselective synthesis of secondary benzylic alcohols

One-pot procedures bear the potential to rapidly build up molecular complexity without isolation and purification of consecutive intermediates. Here, we report multicatalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities (typically >95:5 er) under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Prochiral allylic alcohols can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er, >20:1 dr).

Farnesyl-diphosphate synthase. Interplay between substrate topology, stereochemistry, and regiochemistry in electrophilic alkylations

The absolute stereochemistries of 8-OPP, 9-OPP, and 10-OPP obtained from incubation of bisubstrate analogs 1-OPP and 2-OPP with farnesyl-diphosphate synthase were determined by correlation of ORD spectra with those of synthetic materials. Only one enantiomer was found for each of the enzymatic products. The products from 1-OPP were (S)-8-OPP and (S)-10-OPP, while those from 2-OPP were (R)-8-OPP, (R)-9-OPP, and (R)-10-OPP. Conformational analysis of 1-OPP and 2-OPP, which considers topological limitations imposed by FPP synthase, indicates that the products from the enzymatic reactions are formed from discrete E·S complexes formed from different conformers of the substrates. Overlays of the conformations that give the observed products are consistent with a model where the hydrocarbon moieties occupy a central volume flanked on top and bottom by their diphosphate residues.

INSECT GROWTH REGULATORS-VIII. SYNTHESIS OF A CYCLIC ANALOG OF JUVENILE HORMONE-II

The "true" cyclic analog of JH-II was obtained in a six step synthesis from natural (+)-limonene as starting material.