58769-97-4

Upstream product

• 10458-14-7 (2R,5S)-menthone 
• 109-94-4 formic acid ethyl ester 
• 2516-99-6 3,3,3-Trifluoropropionic acid 
• 110-45-2 isopentyl formate 

Downstream Products

• 190142-54-2 2-methyl-2-formyl-(l)-menthone 
• 1206901-82-7 (1S,3R,6S)-6-isopropyl-3-methyl-2-methylene-cyclohexanol 
• 82425-79-4 (1R,4S)-(+)-methylene-2 p-menthanone-3 
• 190142-56-4 (E)-3-((1R,2R,3S,6R)-2-Hydroxy-3-isopropyl-1,6-dimethyl-2-prop-2-ynyl-cyclohexyl)-acrylic acid ethyl ester 
• 190142-55-3 (E)-3-((1R,3S,6R)-3-Isopropyl-1,6-dimethyl-2-oxo-cyclohexyl)-acrylic acid ethyl ester 

Relevant academic research and scientific papers

Stereocontrolled syntheses of (-)-cubebol and (-)-10-epicubebol involving intramolecular cyclopropanation of a-lithiated epoxides

Figure Presented Formylation of (-)-menthone (11) with LDA and HCO 2CH2CF3 avoids loss of configurational integrity at the isopropyl group, giving hydroxymethylenementhone 12. Lithium 2,2,6,6-tetramethylpiperidideinduced intramolecular cyclopropanation of derived unsaturated terminal epoxide 17 (and chlorohydrin 16), efficiently generates a substituted tricyclo[4.4.0.01.5]decan-4-ol 18, which is used in a concise synthesis of (-)-cubebol (1). In contrast, isopropyl group inversion during formylation of menthone with NaOMe and HCO2Et led, by a similar strategy, to syntheses of 7-epicubebol (33) and (from(+)-menthone) of naturally occurring (-)-10-epicubebol (39), confirming the original structural assignment. Computational studies support the origin of the inversion as being rate-determining formylation of cis-enolate 27 from amixture of rapidly interconverting enolates. In the synthesis of 7-epicubebol (33), allylic tertiary C-H insertion is observed as a significant competing reaction in the intramolecular cyclopropanation of unsaturated terminal epoxide 22.

New optically active pyrazoles: Syntheses and the structural characterization of menthopyrazole analogues

New chiral pyrazoles, (4R,7R)-4-methyl-7-isopropyl-3-phenyl- (3-phenylisomenthopyrazole; cis-1), (4R,7S)-4-methyl-7-isopropyl- (l-menthopyrazole; trans-2), (4R,7R)-4-isopropyl-7-methyl- (isocarvomenthopyrazole, cis-3) and (4R,7S)-4-isopropyl-7-methyl-4,5,6,7-tetrahydro-1H-indazole (carvomenthopyrazole, trans-3) were prepared. The diastereomeric pairs of these 1-3 were structurally characterized by NMR spectroscopy. The subtle differences of structures of 1-3 should induce the useful effects for a chiral auxiliary or a chiral catalyst.