190451-39-9

Upstream product

• 59633-91-9 rac-12-nor-drimane-8α,11-diol 
• 65754-92-9 (+/-)-methyl (1β,2α,4aα,8aβ)-2-formyloxy-decahydro-5,5,8a-trimethylnaphthalene-1-carboxylate 

Downstream Products

• 211053-91-7 (4aR,5S,6S,8aR)-6-Benzyloxy-5-bromomethyl-1,1,4a-trimethyl-decahydro-naphthalene 
• 211053-87-1 ((1R,2S,4aR,8aR)-2-Benzyloxy-5,5,8a-trimethyl-decahydro-naphthalen-1-yl)-methanol 
• 211053-83-7 (-)-(4aR,8aR)-1-(2,5-dimethoxyphenyl)methyl-2-acetoxy-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene 
• 69880-60-0 (+)-zonarol dimethyl ether 
• 108944-90-7 (1S,4aR,8aR)-(+)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene 
• 211053-86-0 (3R,4aS,6aR,10aR,10bR)-7,7,10a-Trimethyl-3-phenyl-decahydro-naphtho[2,1-d][1,3]dioxine 

Relevant academic research and scientific papers

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.

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.