31222-15-8

Upstream product

• 107-21-1 ethylene glycol 
• 160837-40-1 (1S,3S,4aS,8aR)-decahydro-4a-hydroxy-3-isopropenyl-8a-methyl-6-oxo-1-naphthalenecarbonitrile 
• 38419-75-9 (1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol 
• 874807-45-1 (S)-phenyl-[(4aS,8aS)-2-(2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-acetoxy]-acetic acid methyl ester 
• 874807-42-8 (R)-phenyl-[(4aS,8aS)-2-(2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-acetoxy]-acetic acid methyl ester 
• 31207-73-5 2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6, 7,8,8a-octahydronaphthalen-1-yl)ethan-1-ol 

Downstream Products

• 6790-58-5 (-)-ambroxide 
• 68985-11-5 [(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1-yl]acetaldehyde 
• 381729-49-3 3-[(1'S,2'S)-1',3',3'-trimethyl-2'-(3''-oxobutyl)cyclohexyl]-3-oxopropyl acetate 
• 381729-50-6 4-[(1S,6S)-6-(3-iodopropanoyl)-2,2,6-trimethylcyclohexyl]butan-2-one 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF OPTICALLY-ACTIVE COMPOUNDS

A method of preparing enatiomerically enriched 3a,6,6,9a-tetramethyl-dodecahydro-naphtho[2,1-b]furan, formula (I), from (E,E)- homofarnesic acid or (E)-monocyclohomofarnesic acid by (a) reacting firstly with a chiral alcohol, (b) reacting the product of (a) with an acid to cause a first cyclisation, (c) producing an alcohol by reacting the product of (b) with a reducing agent and (d) causing a second cyclisation by reacting the product of (c) with an acid. The product of this process gives a mixture of both enantiomers with one in excess.

Synthesis of Ambrox from labdanolic acid

A synthesis of the valuable amber-type odorant Ambrox from labdanolic acid (main diterpenoid of the acid fraction of non-polar extracts of Cistus ladaniferus L.) is reported. The conversion is based on (a) the α,β-dehydrogenation of methyl labdanolate using an organoselenium reagent, (b) subsequent oxidative degradations of the side chain, and (c) final acid-promoted cyclization of the resulting tetranorlabdan-8α,12-diol. The influence of the temperature and solvent in the cyclization of the diol with p-toluenesulfonic acid is also described. Thus, Ambrox has been obtained by a six-step procedure in 33% overall yield from methyl labdanolate.

Total Synthesis of (-)-Ambrox from S-(+)-Carvone (part 6)

Conjugate addition of cyanide and allyl nucleophiles to S-(+)-carvone followed by annulation with methyl vinyl ketone gave the substituted decalones 2 and 3 stereoselectively.Both decalones were transformed into (-)-Ambrox via modification of the sidechain, methylation, conversion of the isopropenyl group and cyclization.