807360-95-8

Upstream product

• 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 
• 6138-90-5 trans-geranyl bromide 
• 56523-17-2 methyl 3-oxo-7,11-dimethyl-dodeca-6,10-dienoate 
• 108944-86-1 (1R,2S,4aS,8aS)-(+)-methyl 2-hydroxy-5,5,8a-trimethyldecahydronaphthalene-1-carboxylate 
• 59633-91-9 8β-hydroxy-9β-hydroxymethyl-(4α,4β),10β-trimethyl-(trans)-decahydronaphthalene 
• 108944-85-0 (1S,2R,4aR,8aR)-(-)-methyl 2-hydroxy-5,5,8a-trimethyldecahydronaphthalene-1-carboxylate 
• 59633-91-9 rac-12-nor-drimane-8α,11-diol 
• 105387-01-7 5,5,8aβ-trimethyl-4aα,5,6,7,8,8a-hexahydro-2(1H)-naphthalenone 
• 65754-79-2 (+/-)-methyl (1β,2β,4aα,8aβ)-2-hydroxy-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 
• 190388-66-0 (-)-(1S,2R,4aS,8aS)-2-hydroxy-decahydro-5,5,8a-trimethyl-1-naphthylmethanol 
• 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 
• 211053-86-0 (3R,4aS,6aR,10aR,10bR)-7,7,10a-Trimethyl-3-phenyl-decahydro-naphtho[2,1-d][1,3]dioxine 
• 95998-96-2 ((6aS,11aR)-4,4,9,11a-Tetramethyl-1,2,3,4,5,6,7,10,11,11a-decahydro-cyclohepta[a]naphthalen-6a-yl)-methanol 

Relevant academic research and scientific papers

An alternative synthesis of 8-Methylene-4,4,8a-trimethyl-7-oxo-octahydronaphthalene

An alternative synthesis of 8-Methylene-4,4,8a-trimethyl-7-oxo-octahydronaphthalene, which is a potential synthon for the preparation of several terpenoid compounds, is described.

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.

An efficient approach to chiral nonracemic trans- and cis-decalin scaffolds for drimane and labdane synthesis

Optically active trans- and cis-ring junction decalinic intermediates, which represent useful precursors for the synthesis of more complex natural targets, have been conveniently prepared starting from the β-ketoester 2 obtained by standard chemistry from

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.

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.

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.

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.