468-84-8

Usage

Uses

Used in Pharmaceutical Applications:
Djson is used as a therapeutic agent for its potential anti-inflammatory and analgesic properties, which can be beneficial in the treatment of various conditions characterized by inflammation and pain.
Used in Antioxidant Applications:
As an antioxidant, djson is used to protect cells from oxidative stress and damage, which can be helpful in preventing or treating a range of diseases associated with oxidative stress, such as neurodegenerative disorders.
Used in Neuroprotective Applications:
Djson's potential neuroprotective effects make it a candidate for use in applications aimed at protecting the nervous system and preventing neurodegenerative diseases.
Used in Research and Development:
Due to its ongoing research and exploration of biological activities, djson is used in the field of research and development to further understand its potential applications in medicine and other fields.
Used in Cosmetics Industry:
Given its anti-inflammatory and antioxidant properties, djson may also find applications in the cosmetics industry for the development of products aimed at skin health and protection.

Upstream product

• 10266-81-6 (5S,9S,10S)-14,15,16-trisnorlabda-8⁽¹⁷⁾-en-13-oic acid 
• 473-03-0 Ambrein 
• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 
• 10207-79-1 ent-8α-hydroxy-labda-13(16),14-dien 
• 39850-84-5 Acetic acid 1-[2-((1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-decahydro-naphthalen-1-yl)-ethyl]-1-methyl-allyl ester 
• 106462-14-0 sclareol 
• 144102-70-5 (13R,14R)-14-hydroperoxy-13,14-epoxy-15-norlabdan-8α-ol 
• 56-23-5 tetrachloromethane 
• 10028-15-6 ozone 
• 67-64-1 acetone 
• 247905-61-9 C₁₅H₂₆O₂ 
• 80098-19-7 labd-13-en-8α-yl acetate 
• 122745-54-4 (-)-8α,17-epoxy-18-hydroxy-14,15,16-trinorlabdan-13,17-olide 

Downstream Products

• 468-84-8 8-hydroxy-14,15,16-trinor-8ξH,9ξH-labdan-13-oic acid-lactone 
• 52811-58-2 Δ¹¹-ambreinolide 
• 641-91-8 1,2,5-trimethylnaphthalene 
• 10267-25-1 methyl (5S,8R,9R,10S,13S)-8-hydroxylabdan-15-oate 
• 473-03-0 (+)-ambreine 
• 473-03-0 (17R)-ambrein 
• 10281-49-9 2-{(1S,2R,4aR,8aS)-1-[(E)-6-(2,2-Dimethyl-6-methylene-cyclohexyl)-4-methyl-hex-3-enyl]-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-yloxy}-tetrahydro-pyran 
• 87553-46-6 (+/-)-(4aS,4bS,8aS)-2,4b,8,8-tetramethyl-1,2,3,4,4a,4b,5,6,7,8,8a,9-dodecahydrophenathrene-2-ol 
• 106687-36-9 Toluene-4-sulfonic acid (R)-2-methyl-3-((1R,4aS,8aS)-5,5,8a-trimethyl-2-oxo-decahydro-naphthalen-1-yl)-propyl ester 
• 106672-27-9 Toluene-4-sulfonic acid (S)-2-methyl-3-((1R,4aS,8aS)-5,5,8a-trimethyl-2-oxo-decahydro-naphthalen-1-yl)-propyl ester 
• 188539-95-9 2-{(1R,2R,4aS,8aS)-2,5,5,8a-Tetramethyl-1-[(E)-4-methyl-5-(toluene-4-sulfonyl)-pent-3-enyl]-decahydro-naphthalen-2-yloxy}-tetrahydro-pyran 
• 473-03-0 (1R,4aα)-1-[(E)-6-[(S)-2,2-dimethyl-6-methylenecyclohexyl]-4-methyl-3-hexenyl]decahydro-2,5,5,8aβ-tetramethylnaphthalene-2α-ol 

Relevant academic research and scientific papers

PRODUCTS OF THE OZONOLYSIS OF ISOABIENOL

The ozonization of abienol in ethyl acetate in the presence of pyridine or in methanol followed by the reduction of the peroxides by methyl sulfide has given ambreinolide.On reduction of the peroxide products of the ozonolysis of isoabienol in methanol with potassium tetrahydroborate, the main reaction product was 15,16-bisnorlabdane-8,13,14-triol.Dimethyl sulfide first caused the rearrangement of the peroxide products of ozonization with the cleavage of the ordinary C-13-C-14 carbon bond, and then their reduction.

Ozonolysis of alkenes and study of reactions of polyfunctional compounds: LXIV. Synthesis of ambreinolide and 8α,13-Epoxy-14,15,16-trisnorlabd-12-ene proceeding from isoabienol ozonolysis

The ozonolysis of isoabienol in MeOH followed by hydrogenation of the peroxide ozonolysis products on Lindlar catalyst afforded ambreinolide that under treatment with diisobutylaluminum hydride furnished 8α, 13-epoxy-14,15,16-trisnorlabd-12-ene.

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.

New total synthesis of (+)-ambrein

The convergent synthesis of (+)-ambrein 1 was achieved based on a modified Julia coupling reaction between aldehyde 14 corresponding to the left-half A and sulfone 25a or 25b corresponding to the right-half B. Aldehyde 14 was synthesized in 14% overall yield (nine steps) from the enzymatic resolution product, epoxy alcohol (8aS)-2. Sulfone 25a or 25b was synthesized in 11 steps (25a: 41% overall yield, 25b: 56% overall yield) from the enzymatic resolution product, (1S,6S)-2,2-dimethyl-6-hydroxyhexane-1-carboxylate 4.

Total synthesis of (+/-)-syn-copalol.

The labdane diterpene derivative, syn-copalol [(+)-5] is the alcohol part of syn-copalyl diphosphate [(+)-4]. In this paper, racemic (+/-)-5 was synthesized from a known racemic lactone in 8 steps. The current and our previous syntheses provide all four copalol derivatives [(+)-3, (-)-3 and (+/-)-5] which are required for the biosynthetic study of polycyclic diterpenes.

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

Synthesis of (+)-Ambrein

Enantiomerically pure (+)-Ambrein was synthesized from (+)-drimane-8,11-diol prepared via lipase catalyzed kinetic resolution, and easily prepared (i)-γ-cyclogeraniol.

Ambergris compounds from labdanolic acid

Labdanolic acid (Cistus ladaniferus) is transformed into derivatives with amber odor. The strategy used allowed a process in which the oxidative decarboxylation reaction was carried out with the hydroxyl group protected.

INVESTIGATION OF THE PRODUCTS OF THE OZONOLYSIS OF SCLAREOL AND THE PATHWAYS FOR THEIR FORMATION

It has been established that main products of the ozonolysis of sclareol (I) under various conditions are "sclareol oxide" (III), 8α-hydroxy-14,15-bisnorlabdan-13-one (IV), and the new compound (13R,14R)-14-hydroperoxy-13,14-epoxy-14-norlabdan-8α-ol (X), and structure of which has been shown on the basis of its trans-formations.The acid fraction of the ozonation products, the yield of which was low (8percent) included two compounds: sclareolic acid (85percent) and 18α-hydroxy-14,15,16-trisnorlabdan-13-oic acid (3percent).The mechanism for the formation of the above mentioned compounds is discussed.