59633-91-9

Upstream product

• 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 
• 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 
• 59684-77-4 (+/-)-8-oxo-12-nordriman-11-acid methyl ester 
• 65754-92-9 (+/-)-methyl (1β,2α,4aα,8aβ)-2-formyloxy-decahydro-5,5,8a-trimethylnaphthalene-1-carboxylate 
• 17283-81-7 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on 
• 59633-89-5 3-oxo-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pentanoic acid methyl ester 
• 71712-61-3 (2Z,6E)-3-(Diethoxy-phosphoryloxy)-7,11-dimethyl-dodeca-2,6,10-trienoic acid methyl ester 
• 65754-79-2 (+/-)-methyl (1β,2β,4aα,8aβ)-2-hydroxy-decahydro-5,5,8a-trimethylnaphthalene-1-carboxylate 
• 6138-90-5 trans-geranyl bromide 
• 59633-88-4 2-(bromomethyl)-1,3,3-trimethylcyclohex-1-ene 

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 

Relevant academic research and scientific papers

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

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.

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.

Lewis Acid and Photochemically Mediated Cyclization of Olefinic β-Keto Esters

Olefinic β-keto esters 8, 17, and 20, prepared by either carbomethoxylation of the parent ketone or alkylation of the dianion of methyl acetoacetate with the allylic bromide, underwent cyclization with stannic chloride in dichloromethane to give mono- and