31207-73-5

Upstream product

• 38419-75-9 (1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol 
• 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 
• 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 

Downstream Products

• 31222-15-8 2-[(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1-yl]ethanol 
• 6790-58-5 (-)-ambroxide 
• 116163-52-1 2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)acetaldehyde 
• 88902-03-8 (+)-γ-polypodatetraene 
• 470474-43-2 (1'S,2E,4a'S,8a'S)-(+)-5-(1',4',4a',5',6',7',8',8a'-octahydro-2',5',5',8a'-tetramethyl-1'-naphthyl)-2-methyl-1-phenylsulfonyl-2-pentene 
• 470474-44-3 (4aS,5S,8aS)-5-((3E,7E)-5-Benzenesulfonyl-4,8,12-trimethyl-trideca-3,7,11-trienyl)-1,1,4a,6-tetramethyl-1,2,3,4,4a,5,8,8a-octahydro-naphthalene 
• 195702-75-1 1-Phenyl-3-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-propan-2-ol 
• 195703-08-3 2-[3-Oxo-3-phenyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-propyl]-malonic acid di-tert-butyl ester 
• 85611-48-9 (4aR,9aS,9bR)-4a,6,6,9a-tetramethyl-trans-perhydroindano<2,1-c>pyran 
• 378198-07-3 [(E)-(1R,2R)-4-Benzenesulfonyl-8-(2,5-bis-benzyloxy-phenyl)-2,6-dimethyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-oct-6-enyloxy]-tert-butyl-dimethyl-silane 
• 378198-08-4 (2R,3R,7E)-2-(tert-butyldimethylsiliyloxy)-9-(2,5-dibenzyloxyphenyl)-3,7-dimethyl-1-[(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenyl]-7-nonene 
• 378198-09-5 (2R,3R,7E)-9-(2,5-dibenzyloxyphenyl)-3,7-dimethyl-1-[(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenyl]-7-nonen-2-ol 
• 378198-10-8 (2R,3R,7E)-9-(2,5-dihydroxyphenyl)-3,7-dimethyl-1-[(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenyl]-7-nonen-2-ol 
• 1026602-48-1 2-[(E)-(7R,8R)-8-Hydroxy-3,7-dimethyl-9-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-non-2-enyl]-[1,4]benzoquinone 

Relevant academic research and scientific papers

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.

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.