54274-72-5

Usage

Uses

1. Used in Pharmaceutical Industry:
1-Naphthalenepropanol,2-(acetyloxy)-a-ethenyldecahydro-a,2,5,5,8a-pentamethyl-,acetate,(aR,1R,2R,4aS,8aS)(9CI) is used as an intermediate in the synthesis of various bioactive compounds, such as (E)-Labd-13-ene-8,15-diol, which possess antiviral and anticancer activities. Its unique molecular structure allows it to be a key component in the development of new drugs targeting specific diseases.
2. Used in Chemical Synthesis:
In the chemical industry, 1-Naphthalenepropanol,2-(acetyloxy)-a-ethenyldecahydro-a,2,5,5,8a-pentamethyl-,acetate,(aR,1R,2R,4aS,8aS)(9CI) can be utilized as a building block for the creation of more complex molecules with diverse applications. Its versatile structure makes it a valuable asset in the synthesis of novel compounds for various purposes, including materials science, agrochemicals, and specialty chemicals.
3. Used in Research and Development:
Due to its unique structure and potential applications, 1-Naphthalenepropanol,2-(acetyloxy)-a-ethenyldecahydro-a,2,5,5,8a-pentamethyl-,acetate,(aR,1R,2R,4aS,8aS)(9CI) is an important compound for research and development in various scientific fields. It can be used as a starting material or a reference compound in the study of chemical reactions, molecular interactions, and the development of new methodologies in organic chemistry.

Upstream product

• 515-03-7 sclareol 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 

Downstream Products

• 672922-61-1 4-Methoxymethoxy-3-[(E)-3-methyl-5-((4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pent-2-enyl]-benzaldehyde 
• 672922-60-0 {4-Methoxymethoxy-3-[(E)-3-methyl-5-((4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pent-2-enyl]-phenyl}-methanol 
• 1153-34-0 epiambraketal 
• 1153-34-0 epi-8-ambracetal 
• 1153-34-0 ambracetal 
• 10314-42-8 isomanool 
• 1164151-92-1 labda-7,14-dien-13(R)-ol 
• 596-85-0 manool 

Relevant academic research and scientific papers

A short and practical synthesis of (+)-amberketal and (-)-epi-8-amberketal from natural (-)-sclareol

Starting from natural (-)-sclareol (4,) (+)-amberketal (9) and (-)-epi-8-amberketal (10) have been synthesized regioselectively in 4 (24% overall yield) and 5 steps (7% overall yield) respectively, by passing through the same unpurified key intermediate 7b.

Concise synthesis of (+)-subersic acid from (-)-Sclareol

A short and efficient synthesis of (+)-subersic acid in 6 steps with an overall yield of 8.6% from (-)-Sclareol was presented using Mitsunobu reaction and Claisen rearrangement as critical steps. This elegant protocol gave a convenient access to gram scal

Antischistosomal Properties of Sclareol and Its Heck-Coupled Derivatives: Design, Synthesis, Biological Evaluation, and Untargeted Metabolomics

Sclareol, a plant-derived diterpenoid widely used as a fragrance and flavoring substance, is well-known for its promising antimicrobial and anticancer properties. However, its activity on helminth parasites has not been previously reported. Here, we show that sclareol is active against larval (IC50 ≈ 13 μM), juvenile (IC50 = 5.0 μM), and adult (IC50 = 19.3 μM) stages of Schistosoma mansoni, a parasitic trematode responsible for the neglected tropical disease schistosomiasis. Microwave-assisted synthesis of Heck-coupled derivatives improved activity, with the substituents choice guided by the Matsy decision tree. The most active derivative 12 showed improved potency and selectivity on larval (IC50 ≈ 2.2 μM, selectivity index (SI) ≈ 22 in comparison to HepG2 cells), juvenile (IC50 = 1.7 μM, SI = 28.8), and adult schistosomes (IC50 = 9.4 μM, SI = 5.2). Scanning electron microscopy studies revealed that compound 12 induced blebbing of the adult worm surface at sublethal concentration (12.5 μM); moreover, the compound inhibited egg production at the lowest concentration tested (3.13 μM). The observed phenotype and data obtained by untargeted metabolomics suggested that compound 12 affects membrane lipid homeostasis by interfering with arachidonic acid metabolism. The same methodology applied to praziquantel (PZQ)-treated worms revealed sugar metabolism alterations that could be ascribed to the previously reported action of PZQ on serotonin signaling and/or effects on glycolysis. Importantly, our data suggest that compound 12 and PZQ exert different antischistosomal activities. More studies will be necessary to confirm the generated hypothesis and to progress the development of more potent antischistosomal sclareol derivatives.

Intermolecular Anti-Markovnikov Hydroamination of Unactivated Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer

Here we report a catalytic method for the intermolecular anti-Markovnikov hydroamination of unactivated alkenes using primary and secondary sulfonamides. These reactions occur at room temperature under visible light irradiation and are jointly catalyzed by an iridium(III) photocatalyst, a dialkyl phosphate base, and a thiol hydrogen atom donor. Reaction outcomes are consistent with the intermediacy of an N-centered sulfonamidyl radical generated via proton-coupled electron transfer activation of the sulfonamide N-H bond. Studies outlining the synthetic scope (>60 examples) and mechanistic features of the reaction are presented.

A short and efficient synthesis of (+)-totarol

A concise route to multigram quantities of the antibacterial diterpene (+)-totarol (1) is reported. (-)-Sclareol (2) was converted to the target compound 1 using either a six- or a seven-step sequence, while only three steps were required to access (+)-totarol ( 1) starting from (+)-manool (9) or (+)-13-epi-manool (10), respectively. A novel one-pot intramolecular aldol condensation/α-alkylation protocol served as the key operation for streamlining the syntheses of 1. ARKAT-USA, Inc.

Method for the preperation of (+)-totarol

The present invention pertains to a simple route to prepare (+)-Totarol from (-)-Sclareol. As intermediate a compound according to formula (I) is used. Compound (I) is reacted with potassium-tert-butylate, suspended in tert-butanol under a oxygen free atmosphere at the boiling temperature of the mixture; then isopropyl iodide is added and the reaction product (II) is separated; As second step the compound (II) is suspended in acetonitrile and then reacted in an oxygen free atmosphere with a blend of LiBr and CuBr2, heated to reflux to form (+)-Totarol.

Short and efficient synthesis of (+)-subersic acids

An efficient synthesis of (+)-subersic acid, the unnatural enantiomer, has been achieved from sclareol and p-hydroxybenzoic acid.

Oxidative degradation of the sclareol side chain: hemisyntheses of ambergris derivatives using in the key steps palladium complexes or ruthenium tetroxide generated in situ

We report the hemisyntheses of various ambergris-type derivatives: ambraoxide 4, Ambrox 8, 13-methylambraoxide 13, ambraketal 14, norambraketal 15, non-norambraketal 16 and dioxepane 53.Sclareol 12 is used as starting material because it is currently available from Salvia sclarea.The key steps involve an oxidative degradation of the sclareol 12 side chain, using either palladium complexes or ruthenium tetroxide generated in situ. - Keywords: sclareol; Ambrox; ambraoxide; 13-methylambraoxide; ambraketal; norambraketal; nor-norambraketal; farnesylic aldehyde; palladium complex; ruthenium tetroxide generated in situ; oxidative degradation

A short efficient synthesis of ambraketal (four steps) and epiambraketal (five steps) from sclareol

Ambraketal 7 and epiambraketal 8 are synthesized efficiently from sclareol 1. The key intermediate 5 is obtained by a regioselective elimination of ketoacetate 4 resulting from the side chain oxidative degradation of 1 by ruthenium tetroxide generated in situ.

Synthesis of Dodecahydro-3a,6,6,69a-tetramethyl naphthofuran via Alkoxy Radical Fragmentation.

Alkoxy radicals of several sclareol derivatives undergo β-fragmentation reactions to provide decahydro-1-(2-haloethyl)-2,5,5,8a-tetramethyl-2-naphthalenol acetates (9b,c) which are converted to dodecahydro-naphthofuran 5 and ambreinolide 6.