23599-47-5

Usage

Uses

Used in Pharmaceutical Industry:
(5aS)-6,6,9aβ-Trimethyl-5,5aα,6,7,8,9,9a,9bα-octahydronaphtho[1,2-c]furan-3(1H)-one is used as a potential pharmaceutical compound for its unique chemical structure and properties. The presence of the furan ring and the ketone group, along with the trimethyl substituents, may contribute to its biological activity, making it a candidate for the development of new drugs or therapeutic agents.
Used in Chemical Industry:
In the chemical industry, (5aS)-6,6,9aβ-Trimethyl-5,5aα,6,7,8,9,9a,9bα-octahydronaphtho[1,2-c]furan-3(1H)-one may be utilized as a key intermediate or building block in the synthesis of other complex organic molecules. Its specific structural features could be exploited for the creation of novel materials or compounds with tailored properties for various applications, such as in the fields of polymers, dyes, or advanced materials.
Further research and development are necessary to fully understand the potential applications and benefits of (5aS)-6,6,9aβ-Trimethyl-5,5aα,6,7,8,9,9a,9bα-octahydronaphtho[1,2-c]furan-3(1H)-one in these industries and to optimize its synthesis and production methods for practical use.

Upstream product

• 89634-40-2 (1R,4aS,8aS)-1-Hydroxymethyl-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbaldehyde 
• 132982-84-4 4,4,8a-trimethyl-Δ⁸-carbomethoxy-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 
• 34437-62-2 drimendiol 
• 6754-20-7 Polygodial 

Relevant academic research and scientific papers

Probing the Structure-Activity Relationship of the Natural Antifouling Agent Polygodial against both Micro- and Macrofoulers by Semisynthetic Modification

The current study represents the first comprehensive investigation into the general antifouling activities of the natural drimane sesquiterpene polygodial. Previous studies have highlighted a high antifouling effect toward macrofoulers, such as ascidians, tubeworms, and mussels, but no reports about the general antifouling effect of polygodial have been communicated before. To probe the structural and chemical basis for antifouling activity, a library of 11 polygodial analogues was prepared by semisynthesis. The library was designed to yield derivatives with ranging polarities and the ability to engage in both covalent and noncovalent interactions, while still remaining within the drimane sesquiterpene scaffold. The prepared compounds were screened against 14 relevant marine micro- and macrofouling species. Several of the polygodial analogues displayed inhibitory activities at sub-microgram/mL concentrations. These antifouling effects were most pronounced against the macrofouling ascidian Ciona savignyi and the barnacle Balanus improvisus, with inhibitory activities observed for selected compounds comparable or superior to several commercial antifouling products. The inhibitory activity against the microfouling bacteria and microalgae was reversible and significantly less pronounced than for the macrofoulers. This study illustrates that the macro- and microfoulers are targeted by the compounds via different mechanisms.

New radical reactions of S-alkoxycarbonyl xanthates. Total synthesis of (±)-cinnamolide and (±)-methylenolactocin

Irradiation with visible light of S-alkoxycarbonyl xanthates derived from various alcohols gives rise to alkoxycarbonyl radicals with bifurcate reactivity: loss of carbon dioxide leads to deoxygenated derivatives (i.e. alkyl xanthates) whereas intramolecular addition to a suitably located double bond produces lactones; these new reactions were applied to the total synthesis of (±)-cinnamolide and (±)-methylenolactocin.

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.

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.