158930-44-0

Upstream product

• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 74-88-4 methyl iodide 

Downstream Products

• 212185-22-3 (5R,6R)-6-(3,3-diethoxypropyl)-2,6-dimethyl-5-(1-methylethenyl)-2-cyclohexen-1-one 
• 126202-28-6 Acetic acid (E)-(S)-1-((1S,6R)-6-isopropenyl-1,3-dimethyl-2-oxo-cyclohex-3-enyl)-4-methyl-hexa-3,5-dienyl ester 
• 183072-25-5 (1aS,1bR,3aR,4R,5S,7aR,7bR,9aR)-4-(2,5-Bis-methoxymethoxy-3-methyl-benzyl)-9a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-ol 
• 182880-82-6 (1aS,1bR,3aR,4S,5S,7aR,7bR,9aR)-4-(2,5-Bis-methoxymethoxy-3-methyl-benzyl)-9a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-ol 
• 182880-73-5 (5R,6R)-2,6-dimethyl-5-(1-methylethenyl)-6-((E)-4-methyl-5-oxo-3-hexenyl)-2-cyclohexen-1-one 
• 182880-75-7 (5R,6R)-6-[(E)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-hexa-3,5-dienyl]-5-isopropenyl-2,6-dimethyl-cyclohex-2-enone 
• 183072-24-4 3-[(1R,6R)-1,3-dimethyl-6-(1-methylethenyl)-2-oxo-3-cyclohexenyl]-1-propanal 
• 75657-53-3 stypodiol 
• 307928-72-9 (5R,6S)-6-[(S)-1-Hydroxy-2-(3-methyl-1,1-dioxo-2,5-dihydro-1H-1λ⁶-thiophen-2-yl)-ethyl]-5-isopropenyl-2,6-dimethyl-cyclohex-2-enone 
• 126202-27-5 (5R,6S)-6-((E)-(S)-1-Hydroxy-4-methyl-hexa-3,5-dienyl)-5-isopropenyl-2,6-dimethyl-cyclohex-2-enone 

Relevant academic research and scientific papers

An Expeditious and Enantioselective Entry to the ABC Ring of the Quassinoid Skeleton

The tricycle (5) with two trans-fused angular methyl groups is constructed from tiglic aldehyde and (S)-carvone involving a stereocontrolled aldol reaction and an endo-selective intramolecular Diels-Alder (IMDA) reaction; the stereochemistry was established by an X-ray study.

An efficient stereoselective synthesis of stypodiol and epistypodiol

An efficient synthesis of stypodiol (1) and its epimer at C-14, epistypodiol (2), was accomplished starting from (S)-(+)-carvone (7). The synthesis of both epimeric compounds proceeds through common intermediates using an IMDA reaction, a sonochemical Barbier reaction, and an acid- catalyzed quinol-tertiary alcohol cyclization as key synthetic steps.

SYNTHETIC STUDY TOWARDS THE TETRACYCLIC QUASSINOID SKELETON

The optically active tetracycle (6) with two trans-fused angular methyl groups is constructed from tiglic aldehyde and (S)-carvone in 9 steps involving a stereocontrolled aldol reaction and an endo-selective intramolecular Diels-Alder (IMDA) reaction.