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• 67594-76-7 (5aR,9aR,9bS)-6,6,9a-Trimethyl-1,3,5,5a,6,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-1-ol 
• 97914-92-6 Methyl <1β, 4aα, 8aβ, 2(1')α>-octahydro-5,5,8a-trimethylnaphthalene-2(1H)-spiro-2'-oxirane-1-carboxylate 
• 71558-03-7 (1R,4aS,8aS)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde 
• 87570-43-2 1-(2,6,6-Trimethyl-cyclohex-1-enyl)-2-trimethylsilanyl-ethanol 
• 71558-02-6 4,4,8a-trimethyl-7,8-dicarbomethoxy-trans-octahydronaphthalene 
• 22567-27-7 (4aRS,5SR,8aRS)-<1,2,3,4,5,8,8a-octahydro-6-(hydroxymethyl)-1,1,4a-trimethylnaphthalen-5-yl>methanol 
• 71557-96-5 dimethyl 3,5,6,7,8,8a-hexahydro-5,5,8a-trimethylnaphthalene-1,2-dicarboxylate 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 5293-90-3 1,3,3-trimethyl-2-vinylcyclohexene 
• 79679-67-7 dimethyl (4aRS,5RS)-1,2,3,4,4a,5-hexahydro-1,1,4a-trimethylnaphthalene-5,6-dicarboxylate 
• 79679-69-9 Methoxycarbonyl-1 trimethyl-5,5,8a octahydro-1,4,4a,5,6,7,8,8a Naphtalenemethanpl-2,-(1RS,4aSR,8aSR) 
• 81752-92-3 (8aS)-(+)-albicanyl acetate 
• 54632-04-1 (8aS)-(+)-albicanol 
• 71558-04-8 [(1R,4aS,8aS)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-methanol 

Relevant academic research and scientific papers

Preparation of 9α-fluorinated sesquiterpenic drimanes and evaluation of their antifeedant activities

The preparation of 9α-fluoro analogues of both natural and unnatural drimane-type sesquiterpenes is described. Their synthesis began with the initial preparation of methyl 8-keto-12-nordriman-11-oate from β-ionone and entailed the electrophilic fluorination of C-9 for the stereoselective introduction of the fluorine atom. The drimane skeleton was completed from, the intermediate 9α-fluoro-8-keto-12-nordrimane system by means of different reactions at the C-8 ketone carbonyl group, essentially Wittig methylenation, cyanohydrin formation or palladium-catalysed carbonylation of the corresponding enol triflate. Further manipulation of the functionalization derived from these key reactions allowed the preparation, among others, of 9α-fluorodrimanes, which are structurally and functionally related to albicanic acid, drimenin and olepupuane. Also described are the reactivities of some of the fluorine-containing systems prepared and a comparative study of the antifeedant activities of a selection of 9α-fluorodrimanes and the corresponding hydrogen analogues against several, insect species with different feeding ecologies (Spodoptera littoralis, Myzus persicae and Rhopalosiphum padi), which revealed a significant increase in the antifeedant activities of some of the fluorinated drimane analogues.

The structure of laricinolic acid and its biomimetic transformation into officinalic acid

Laricinolic acid (8), a new sesquiterpene of the drimane type, has been isolated from the wood-rotting fungus Laricifomes officinalis. Its structure was elucidated by spectroscopic means and confirmed via a correlation with the known drimenine derivative 13. Oxidation of 8 to 1, followed by a mild thermal treatment, furnished (-)-officinalic acid (4) in 65% yield. This transformation establishes the hitherto unknown absolute configuration of the latter. An independent correlation was achieved by pyrolysis of 4 which furnished (-)-dihydrooxoisodrimenine (14) of known absolute configuration.

A convenient synthesis of (+)-albicanol based on enzymatic function: Total syntheses of (+)-albicanyl acetate, (-)-albicanyl 3,4- dihydroxycinnamate, (-)-drimenol, (-)-drimenin and (-)-ambrox

By using lipase 'PL-266' from Alcaligenes sp. enantioselective acetylation of (±)-albicanol 4 with isopropenyl acetate gave the enantiomerically pure (+)-albicanyl acetate 3 and (+)-albicanol 4. Deprotection of (+)-3 afforded the natural (+)-albicanol 4 which was converted to the natural products (-)-albicanyl 3,4-dihydroxycinnamate 7, (- )-drimenol 8, (-)-drimenin 9 and (-)-ambrox 10. (C) 2000 Elsevier Science Ltd.

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.