65754-93-0

Upstream product

• 59684-77-4 (+/-)-8-oxo-12-nordriman-11-acid methyl ester 
• 59633-89-5 3-oxo-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pentanoic acid methyl ester 
• 17283-81-7 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on 
• 65754-79-2 (+/-)-methyl (1β,2β,4aα,8aβ)-2-hydroxy-decahydro-5,5,8a-trimethylnaphthalene-1-carboxylate 
• 65754-92-9 (+/-)-methyl (1β,2α,4aα,8aβ)-2-formyloxy-decahydro-5,5,8a-trimethylnaphthalene-1-carboxylate 
• 49749-46-4 1-methoxycarbonyl-2-oxo-1β,2,3,4,4aα,5,6,7,8aβ-octahydro-5,5,8a-trimethylnaphthalene 
• 65754-79-2 (+/-)-methyl (1α,2β,4aα,8aβ)-2-hydroxy-decahydro-5,5,8a-trimethylnaphthalene-1-carboxylate 
• 65754-79-2 (+/-)-methyl (1α,2α,4aα,8aβ)-2-hydroxy-decahydro-5,5,8a-trimethylnaphthalene-1-carboxylate 
• 56523-17-2 methyl 3-oxo-7,11-dimethyl-dodeca-6,10-dienoate 
• 71712-61-3 (2Z,6E)-3-(Diethoxy-phosphoryloxy)-7,11-dimethyl-dodeca-2,6,10-trienoic acid methyl ester 

Downstream Products

• 190451-39-9 (1R,2S,4aR,8aR)-2-hydroxy-decahydro-5,5,8a-trimethyl-1-naphthylmethanol 
• 301323-26-2 Acetic acid 5-methoxy-2-((3S,4aR,6aS,10aS,10bS)-7,7,10a-trimethyl-decahydro-naphtho[2,1-d][1,3]dioxin-3-yl)-phenyl ester 
• 108944-90-7 (1S,4aR,8aR)-(+)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene 
• 69880-60-0 (+)-zonarol dimethyl ether 
• 190388-66-0 (-)-(1S,2R,4aS,8aS)-2-hydroxy-decahydro-5,5,8a-trimethyl-1-naphthylmethanol 
• 211053-77-9 Acetic acid (1S,2R,4aS,8aS)-2-benzyloxy-5,5,8a-trimethyl-decahydro-naphthalen-1-ylmethyl ester 
• 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 

Relevant academic research and scientific papers

Studies in lipase catalyzed transesterifications: Synthesis of (+)- albicanol, (+)-albicanyl acetate and chiral intermediates useful in the synthesis of drimanes and labdanes

Chiral intermediates [(-)-8, (+)-9, (-)-9, (+)-10, (-)-10, (+)-11] useful in the synthesis of drimanes and labdanes, as well as optically active albicanol 1 and albicanyl acetate 2, have been synthesized using enzymatic transesterification as the key step. (C) 2000 Elsevier Science Ltd.

Synthesis of decalin type chiral synthons based on enzymatic function

Enzymatic monobenzoylation of (±)-2-hydroxy-decahydro-5,5,8a-trimethyl-1-naphthalenemethanol derivatives (1 - 4) using vinyl benzoate in organic solvent gave the optically active diols (1 - 4) and monobenzoates (16 - 19). The enantiomeric excess (ee) of t

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.

STUDIES TOWARD THE TOTAL SYNTHESIS OF POLYOXYGENATED LABDANES: PRELIMINARY APPROACHES

Using the keto-ester 3 as a starting material, methods are developed for the successive introduction of hydroxy groups at C-6, C-7 and C-8 of a decalin system, as well as for elaboration of a C-9 pentadiene chain in preliminary approach to the total synthesis of trihydroxylabdadienes.

A formal synthesis of (±)-Ambrox

Bicyclic diol 6, a direct precursor of (±)-Ambrox ((±)-7), has been synthesised in four steps (35% yield) from the known bicyclic enone 2.