190388-66-0

Upstream product

• 65754-92-9 (+/-)-methyl (1β,2α,4aα,8aβ)-2-formyloxy-decahydro-5,5,8a-trimethylnaphthalene-1-carboxylate 
• 65754-79-2 (+/-)-methyl (1β,2α,4aα,8aβ)-2-hydroxydecahydro-5,5,8a-trimethylnaphthalene-1-carboxylate 
• 190388-64-8 Methyl 7,11-Dimethyldodeca-2,6,10-trienoate 
• 59633-91-9 rac-12-nor-drimane-8α,11-diol 
• 190388-82-0 methyl (1R,2R,4aS,8aS)-2-hydroxydecahydro-5,5,8a-trimethylnaphthalene-1-carboxylate 

Downstream Products

• 6790-58-5 (-)-ambroxide 
• 211053-79-1 (-)-(1R,2S,4aS,8aS)-2-benzyloxy-1-bromomethyl-decahydro-5,5,8a-trimethylnaphthalene 
• 211053-77-9 Acetic acid (1S,2R,4aS,8aS)-2-benzyloxy-5,5,8a-trimethyl-decahydro-naphthalen-1-ylmethyl ester 
• 211053-75-7 (-)-(1S,2R,4aS,8aS)-2-benzyloxydecahydro-5,5,8a-trimethyl-1-naphthylmethanol 
• 211053-74-6 [(3S,4aR,6aS,10aS,10bS)-decahydro-7,7,10a-trimethyl-1H-naphtho[2,1-d][1,3]dioxin-3-yl]benzene 

Relevant academic research and scientific papers

Synthesis of decalin type chiral synthons based on enzymatic functionalisation and their application to the synthesis of (-)-ambrox and (+)-zonarol

Stereoselective syntheses of (-)-ambrox 2 and (+)-zonarol 3 were achieved based on the enzymatic syntheses of (8aS)- and (8aR)-decalin-type 1,3-diols 1, respectively. Non-racemic intermediates such as (8aS)-1 and (8aR)-1 were obtained based on the enantioselective hydrolyses of the phenolic acetal derivative (±)-7 by acylase I.

Simple approach to optically active drimane sesquiterpenes based on enzymatic resolution

When the β-acyloxy esters (±)-10 and (±)-II were exposed to the lipase OF-360 from Candida rugosa or immobilized lipase OF-360 in a water- saturated organic solvent, the hydrolyzed product (8aS)-6 was obtained in high chemical (40%) and optical (>99%ee) yields. The absolute structure of (8aS)-6 was confirmed by the fact that (8aS)-6 was converted into an authentic sample γ-keto nitrile (8aS)-17. Treatment of the diol (±)-12 with isopropenyl acetate in the presence of the lipase Godo E-4 from Pseudomonas sp. provided the unchanged (8aR)-12 (89% ee) in 42% yield.