108944-88-3

Upstream product

• 108888-66-0 (1R,2S,4aS,8aS)-5,5,8a-Trimethyl-2-((R)-1-naphthalen-1-yl-ethylcarbamoyloxy)-decahydro-naphthalene-1-carboxylic acid methyl ester 
• 3796-70-1 trans geranyl acetone 
• 59633-91-9 8β-hydroxy-9β-hydroxymethyl-(4α,4β),10β-trimethyl-(trans)-decahydronaphthalene 
• 59684-77-4 (+/-)-8-oxo-12-nordriman-11-acid methyl ester 
• 59684-77-4 (1R,4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-1-methoxycarbonyl-5,5,8a-trimethyl-trans-naphthalene-2(1H)-one 
• 314049-55-3 (1S,2S,4aS,8aS)-2-hydroxy-5,5,8a-trimethyldecahydronaphthalen-1-ylmethyl (S)-1-tert-butoxycarbonyl-pyrrolidine-2-carboxylate 
• 108944-86-1 (1R,2S,4aS,8aS)-(+)-methyl 2-hydroxy-5,5,8a-trimethyldecahydronaphthalene-1-carboxylate 
• 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 
• 56523-17-2 methyl 3-oxo-7,11-dimethyl-dodeca-6,10-dienoate 
• 65754-79-2 (+/-)-methyl (1β,2β,4aα,8aβ)-2-hydroxy-decahydro-5,5,8a-trimethylnaphthalene-1-carboxylate 
• 71712-61-3 (2Z,6E)-3-(Diethoxy-phosphoryloxy)-7,11-dimethyl-dodeca-2,6,10-trienoic acid methyl ester 
• 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 

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 
• 10395-37-6 methyl ent-labda-8⁽¹⁷⁾,13-E-dien-15-oate, methyl copalate 
• 108944-88-3 (1S,2S,4aS,8aS)-(-)-1-hydroxymethyl 2-hydroxy-5,5,8a-trimethyldecahydronaphthalene 
• 108944-87-2 (1R,2R,4aR,8aR)-(-)-1-hydroxymethyl-2-hydroxy-5,5,8a-trimethyldecahydronaphthalene 
• 30801-12-8 methyl (5S,9S,10S,13E)-labda-8⁽¹⁷⁾,13-dien-15-oate 
• 108944-91-8 (1R,4aS,8aS)-(-)-1-(2,5-dimethoxyphenyl)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene 
• 108944-92-9 (-)-zonarol dimethyl ether 
• 59633-93-1 (1S,4aS,8aS)-(-)-1-(p-tosyloxy)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene 

Relevant academic research and scientific papers

Total synthesis of two 12-nordrimanes and the pharmacological active sesquiterpene hydroquinone yahazunol

The synthesis of two 12-nordrimanes and yahazunol was achieved via 8-oxo-12-nordrimanic acid methyl ester. The cytotoxic activity of yahazunol and seven other sesquiterpene hydroquinones and sesquiterpene quinones has been determined.

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

Total synthesis of both enantiomers of copalol via optical resolution of a general synthetic intermediate for drimane sesquiterpenes and labdane diterpenes

The total synthesis of both enantiomers of copalol (6) was accomplished via the optical resolution of a racemic diol [(±)-4] which is a general synthetic intermediate for drimane sesquiterpenes and labdane diterpenes. Esterification between (±)-4 and Boc-L-proline gave the diastereomeric pair of monoesters (5a and 5b) which could be readily separated by flash column chromatography. PDC-oxidation of the resolved 5a and 5b, and subsequent β-elimination gave optically active enones (9 and ent-9). Both enones were respectively converted into (+)-6 in 36% yield and (-)-6 in 26% yield in five steps: (1) Sakurai reaction (TiC14-promoted conjugate addition of allylsilane), (2) Wittig methylenation, (3) Wacker oxidation, (4) Horner-Emmons reaction, and (5) DIBAL-H reduction. (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.