33118-34-2

Usage

InChI:InChI=1/C15H22O2/c1-14(2)7-4-8-15(3)12(10-17)11(9-16)5-6-13(14)15/h5,9-10,12-13H,4,6-8H2,1-3H3/t12-,13-,15+/m1/s1

Upstream product

• 71558-02-6 4,4,8a-trimethyl-7,8-dicarbomethoxy-trans-octahydronaphthalene 
• 56666-27-4 3,4,4aα,5,6,7,8,8aβ-octahydro-5,5,8aβ-trimethyl-3-oxonaphthalene-2-carboxaldehyde 
• 71557-96-5 dimethyl 3,5,6,7,8,8a-hexahydro-5,5,8a-trimethylnaphthalene-1,2-dicarboxylate 
• 361544-76-5 5,5,8a-Trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-1,2-dicarboxylic acid dimethyl ester 
• 71558-02-6 Dimethoxy carbonyl-1,2 trimethyl-5,5,8a Octahydro-1,4,4a,5,6,7,8,8a naphtalene-(1RS, 4aSR, 8aRS) 
• 22567-27-7 ((1S,4aR,8aS)-2-Hydroxymethyl-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-methanol 
• 5956-39-8 (1S,4aR,8aS)-5,5,8a-Trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1,2-dicarbaldehyde 
• 79679-67-7 (S)-5,5,8a-Trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-1,2-dicarboxylic acid dimethyl ester 
• 71558-02-6 (1S,4aS)-5,5,8a-Trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1,2-dicarboxylic acid dimethyl ester 
• 79679-67-7 dimethyl (4aRS,5RS)-1,2,3,4,4a,5-hexahydro-1,1,4a-trimethylnaphthalene-5,6-dicarboxylate 
• 87570-43-2 1-(2,6,6-Trimethyl-cyclohex-1-enyl)-2-trimethylsilanyl-ethanol 
• 71493-15-7 2-(1,3-dioxolan-2-yl)-1,4,4aα,5,6,7,8,8a-octahydro-5,5,8aβ-trimethylnaphthalene-1α-corboxaldehyde 
• 112320-77-1 2(E)-<(butylthio)methylene>-5,5,8aβ-trimethyl-trans-perhydro-3-oxonaphthalene-1α-carbonitrile 
• 112320-79-3 2-(1,3-dioxolan-2-yl)-1,4,4aα,5,6,7,8,8a-octahydro-5,5,8aβ-trimethylnaphthalene-1α-carbonitril 

Downstream Products

• 71536-99-7 isotadeonal 
• 5956-39-8 (1R,4aR,8aS)-5,5,8a-Trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1,2-dicarbaldehyde 

Relevant academic research and scientific papers

Synthesis of all possible stereoisomers of polygodial

The three possible isomers of polygodial, epimers at C-9, cis and trans fused, are described.Controlled kinetic and thermodynamic epimerizations allow preparation of all stereoisomers from the same key intermediate.

The Diels-Alder Route to Drimane related Sesquiterpenes; Synthesis of Cinnamolide, Polygodial, Isodrimeninol, Drimenin and Warburganal

The stereospecific preparation of various 1-vinyl-2,6,6-trimethylcyclohex-1-enes (6) as potential diene precursors in the Diels-Alder reaction with dimethyl acetylenedicarboxylate have been investigated.The reaction of the parent diene (6a) with dimethyl acetylenedicarboxylate affords an adduct (18) in 94percent yield.This species was reductively isomerised using 10percent Pd/C/H2 and a mineral acid to give a trans-fused decalin diester (19).Reduction of (19) with lithium aluminium hydride afforded 1,4,4a,5,6,8,8a-octahydro-5,8,8a-trimethyl-1β,4aα,8aβ-naphthalene-1,2-dimethanol (24) a key starting material for the highly efficient syntheses of five drimane sesquiterpene natural products, cinnamolide (1), polygodial (2), isodrimeninol (3), drimenin (4), and warbuganal (5).Microbial oxidation reactions using C. elegans or A. niger of (2), (24), and (1) gave good yields of the corresponding 3β-hydroxy derivatives, (30), (31), and (32).Several other unusually substituted drimane derivatives are reported.

SYNTHESE TOTALE DU (+/-)POLIGODIAL, DE LA DRIMENINE ET DE COMPOSES APPARENTES A JONCTION DE CYCLE cis ET trans

Isomerization by base under kinetic or thermodynamic control of the Diels-Alder adduct of 1,3,3-trimethyl-2-vinyl-1-cyclohexene with dimethyl acetylene dicarboxylate leads to two isomers which, after catalytic hydrogenation, give in high yield starting materials for synthesis of trans and cis drimanes.A short total synthesis of (+/-)-polygodial and (+/-)-drimenine from one of these isomers is desribed.

EFFICIENT TOTAL SYNTHESES OF POLYGODIAL AND DRIMENIN.

A short and stereoselective total synthesis of (+/-) polygodial and drimenin is presented.The efficiency of the synthesis is due to the easy access to intermediate diol 4 and its successful direct oxidation into polygodial.

Synthesis of Cinnamolide and Polygodial

Starting from 2,6,6-trimethyl-1-vinylcyclohex-1-ene a short synthesis of the sesquiterpenes cinnamolide and polygodial has been achieved with 60 percent and 57 percent overall yields, respectively.