6790-58-5

Usage

Preparation

Ambroxene naturally occurring autoxidation or photooxide of the triterpenoid secreted by sperm whales.Industrially, High acacia acid was prepared from nerolidol. After acid internal esterification, the racemic Ambroxene was obtained.Ambroxide is synthesized from sclareol, a component of the essential oil of clary sage. Sclareol is oxidatively degraded to a lactone, which is hydrogenated to the corresponding diol. The resulting compound is dehydrated to form ambroxide.

Flammability and Explosibility

Notclassified

Side effects

The most common side effects associated with Ambroxane use include those which are observed among patients developing allergic reactions. These include pruritus, hives, and swelling in the face, lips, tongue, or throat. It is important to immediately seek medical attention upon the development of dangerous adverse allergic reactions like difficulty in breathing, shortness of breath, convulsions, and mood changes.

Synthesis

Perillyl alcohol is used as raw material to synthesize nordrone ether, which is oxidized by KMnO4 in two steps (Switzerland uses ozone oxidation, Russia uses sodium chromate oxidation). That is (1) alkaline oxidation; (2) weak acid oxidation. The oxide is obtained, and then the oxide is soaped, dehydrated and lactonized to obtain ambroxolide. lactones are reduced to ambroxol with lithium aluminum hydride in ether (or with borane in tetrahydrofuran). D-camphor-β-sulfonic acid is used as a cyclizing agent to cyclize diols to obtain ambrox (foreign cyclizing agents include sulfuric acid, p-toluenesulfonic acid and β-naphthalenesulfonic acid, etc.).

InChI:InChI=1/C16H28O/c1-14(2)8-5-9-15(3)12(14)6-10-16(4)13(15)7-11-17-16/h12-13H,5-11H2,1-4H3

Synthetic route

(3aR)-(+)-sclareolide (564-20-5, 1216-84-8, 30450-17-0, 58976-28-6, 64090-92-2, 67844-42-2, 79768-41-5, 79768-42-6, 86688-27-9, 86688-28-0, 95406-08-9, 98719-44-9, 98719-46-1, 131831-65-7, 140851-80-5) → (1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (38419-75-9) + (-)-ambroxide (6790-58-5)

Conditions	Yield
With RuCl2(2-(diphenylphosphino)-N-(thiophen-2-ylmethyl)ethanamine)PPh3; hydrogen In toluene at 100℃; under 37503.8 Torr; for 16h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Autoclave;	A 99.5% B n/a
With RuCl2(2-(diphenylphosphino)-N-(2-(methylthio)ethyl)ethanamine)PPh3; hydrogen; sodium methylate In toluene at 100℃; for 16h; Catalytic behavior; Autoclave;	A 67% B 12%

biscyclohomofarnesane-8α,12-diol (320756-17-0) → (-)-ambroxide (6790-58-5)

Conditions	Yield
With ammonium cerium(IV) nitrate In acetonitrile at 20℃; for 11h;	98%

(8α-Methyl)-iresan-8β,11-diol (10207-83-7, 38419-75-9, 41747-05-1, 55881-96-4, 64090-93-3, 86023-44-1, 86023-45-2, 100679-84-3, 105087-83-0, 106035-74-9, 106091-98-9, 106091-99-0, 122566-14-7, 131831-64-6, 131831-66-8, 131831-67-9, 131831-74-8) → (-)-ambroxide (6790-58-5)

Conditions	Yield
With ammonium cerium(IV) nitrate In acetonitrile at 20℃; for 10h;	97%

(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (38419-75-9) → (-)-ambroxide (6790-58-5)

Conditions	Yield
With n-butyllithium; p-toluenesulfonyl chloride In tetrahydrofuran; hexane at 0 - 20℃;	96%
With sodium hydride; p-toluenesulfonyl chloride In dichloromethane at 25℃;	94%
With zinc(II) chloride In 1,2-dichloro-ethane for 3h;	92%

Δ2(3)-ambrox (1038482-07-3) → (-)-ambroxide (6790-58-5)

Conditions	Yield
With 10% Pd/C; hydrogen In ethyl acetate at 20℃; for 12h;	96%
With palladium 10% on activated carbon; hydrogen In methanol under 760.051 Torr;	92%

aqueous sodium sulfate + (1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (38419-75-9) → (-)-ambroxide (6790-58-5)

Conditions	Yield
With hydrogenchloride In water; toluene	95%

<1R-(1α,2β,4aβ,8aα)>-decahydro-1-(2-chloroethyl)-2,5,5,8a-tetramethyl-2-naphthalenol acetate (121067-50-3) → (-)-ambroxide (6790-58-5)

Conditions	Yield
With potassium hydroxide In water; isopropyl alcohol	92%

(3aS,5aS,9aS,9bR)-3a,6,6,9a-Tetramethyl-decahydro-naphtho[2,1-b]furan-4-one (116163-57-6) → (-)-ambroxide (6790-58-5)

Conditions	Yield
With potassium hydroxide; hydrazine	90%

(3aR)-(+)-sclareolide (564-20-5, 1216-84-8, 30450-17-0, 58976-28-6, 64090-92-2, 67844-42-2, 79768-41-5, 79768-42-6, 86688-27-9, 86688-28-0, 95406-08-9, 98719-44-9, 98719-46-1, 131831-65-7, 140851-80-5) → (-)-ambroxide (6790-58-5)

Conditions	Yield
With sodium tetrahydroborate; zinc(II) iodide In tetrahydrofuran for 1h; Heating;	85%
Multi-step reaction with 2 steps 1: 95 percent / potassium borohydride / ethanol / 10 h / Heating 2: 92 percent / bromotrichloromethane; triphenylphosphine; NaHCO3 / CH2Cl2 / 6 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 97 percent / LiAlH4 / tetrahydrofuran / 3 h / 20 °C 2: 96 percent / n-BuLi; TsCl / hexane; tetrahydrofuran / 0 - 20 °C View Scheme

<1R-(1α,2β,4aβ,8aα)>-1-decahydro-1-(2-iodoethyl)-2,5,5,8a-tetramethyl-2-naphthalenol acetate (121067-46-7) → (-)-ambroxide (6790-58-5)

Conditions	Yield
With potassium hydroxide In water; isopropyl alcohol for 18h; Heating;	81%

2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6, 7,8,8a-octahydronaphthalen-1-yl)ethan-1-ol (31207-73-5) → 2-[(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1-yl]ethanol (31222-15-8) + (-)-ambroxide (6790-58-5)

Conditions	Yield
With toluene-4-sulfonic acid In nitromethane for 18h; Ambient temperature;	A n/a B 80%

2-[(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1-yl]ethanol (31222-15-8) → (-)-ambroxide (6790-58-5)

Conditions	Yield
With iron(III) chloride In 1,2-dichloro-ethane at 25℃; Reagent/catalyst; enantioselective reaction;	77%
Acidic conditions;

13,14,15,16-tetranor-8βH-labdane-8,12-diol (41747-05-1) → (-)-ambroxide (6790-58-5)

Conditions	Yield
With toluene-4-sulfonic acid In nitromethane at 80℃; for 0.5h;	76%
With toluene-4-sulfonic acid In nitromethane at 40℃; for 0.0833333h;	45%

8α,12-epoxy-13,14,15,16-tetranorlabdan-19-al (152185-80-3) → (-)-ambroxide (6790-58-5)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate In various solvent(s) for 1h; Heating;	71%
With potassium hydroxide; hydrazine hydrate In various solvent(s) for 1h; Heating;	71%

(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-yl acetate (38419-76-0) → (1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (38419-75-9) + (-)-ambroxide (6790-58-5)

Conditions	Yield
With sodium methylate; carbonic acid dimethyl ester In tetrahydrofuran; methanol at 65℃; for 2h;	A 4% B 67%

<1S-(1α,2β,3β,4β,4aβ,8aα)> decahydro-3-hydroxyl-2,5,5,8a-tetramethylnaphthalene-1-ethanol (158577-90-3) → (-)-ambroxide (6790-58-5) + 8β,12-epoxy-13,14,15,16-tetranorlabdane (68365-88-8)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 80℃; for 2h;	A 48% B 10%

(1R,2R,4aS,8aS)-1-(3-Hydroperoxy-3-methyl-pent-4-enyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol (105735-95-3, 105735-96-4) → (-)-ambroxide (6790-58-5)

Conditions	Yield
With copper diacetate; iron(II) sulfate In methanol at 50℃; for 3h;	33%
With copper diacetate; iron(II) sulfate In methanol at 50℃; for 3h; Product distribution; other amounts of reagents;
Multi-step reaction with 4 steps 1: triphenylphosphine / diethyl ether / 24 h / 20 °C 2: 83 percent / H2 / 5percent Pd/C / ethanol / 760 Torr / Ambient temperature 3: 1.) aq. NaOCl / 1.) AcOH, CCl4, 0 deg C, 3h, 2.) 30-35 deg C, 3h 4: 80percent NaH / tetrahydrofuran / 3 h / Heating View Scheme

sclareol (515-03-7) → (-)-ambroxide (6790-58-5)

Conditions	Yield
With dihydrogen peroxide In water at 70℃; for 4h;	20%
Multi-step reaction with 2 steps 1.1: potassium permanganate; acetic anhydride / acetone / 2 h / 0 °C 1.2: 97 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C 2.1: 92 percent / bromotrichloromethane; triphenylphosphine; NaHCO3 / CH2Cl2 / 6 h / Heating View Scheme
Multi-step reaction with 6 steps 1.1: peracetic acid; NaOAc / ethyl acetate / 192 h / 20 °C 2.1: 1 N aq. NaOH / 2-methyl-propan-2-ol / 20 °C 2.2: H2SO4 / ethyl acetate / 2 h / 0 - 20 °C 3.1: 97 percent / NaIO4 / tetrahydrofuran; H2O / 16 h / 20 °C 4.1: 95 percent / peracetic acid / 50 - 55 °C 5.1: 97 percent / LiAlH4 / tetrahydrofuran / 3 h / 20 °C 6.1: 96 percent / n-BuLi; TsCl / hexane; tetrahydrofuran / 0 - 20 °C View Scheme

C20H39N2O3P (113327-33-6) → (-)-ambroxide (6790-58-5)

Conditions	Yield
With lithium In various solvent(s) Yield given;

(1R,2R,4aS,8aS)-1-(2-Chloro-ethyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol (113105-33-2) → (-)-ambroxide (6790-58-5)

Conditions	Yield
With sodium hydride In tetrahydrofuran for 3h; Heating; Yield given;

Toluene-4-sulfonic acid 2-((1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-decahydro-naphthalen-1-yl)-ethyl ester → (-)-ambroxide (6790-58-5)

Conditions	Yield
for 1h; Ambient temperature; Yield given;

(4aS,6aR,11aR,11bS)-4,4,6a,11b-Tetramethyl-dodecahydro-7,9-dioxa-cyclohepta[a]naphthalene (38419-77-1) → (-)-ambroxide (6790-58-5)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane

(4aS)-1t-<2-hydroxy-ethyl>-2t,5,5,8a-tetramethyl-(4ar,8at)-decahydro-<2c>naphthol → (-)-ambroxide (6790-58-5)

(4aS)-1t(?)-<2-hydroxy-ethyl>-2c(?),5,5,8a-tetramethyl-(4ar,8at-decahydro-<2t?>naphthol → (-)-ambroxide (6790-58-5) + 8β,12-epoxy-13,14,15,16-tetranorlabdane (68365-88-8)

Conditions	Yield
With naphthalene-2-sulfonate Erhitzen unter vermindertem Druck;

(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (38419-75-9) → 2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6, 7,8,8a-octahydronaphthalen-1-yl)ethan-1-ol (31207-73-5) + 2-[(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1-yl]ethanol (31222-15-8) + (-)-ambroxide (6790-58-5)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane for 0.5h; Heating; Title compound not separated from byproducts;	A 7.2 % Chromat. B 16.8 % Chromat. C 67.4 % Chromat.
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 1h; Title compound not separated from byproducts;	A 7.6 % Chromat. B 16.8 % Chromat. C 65.2 % Chromat.

(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (38419-75-9) → 2-[(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1-yl]ethanol (31222-15-8) + (-)-ambroxide (6790-58-5) + 8β,12-epoxy-13,14,15,16-tetranorlabdane (68365-88-8)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane for 30h; Heating; Title compound not separated from byproducts;	A 11.2 % Chromat. B 29.6 % Chromat. C 59.1 % Chromat.

(E,E)-homofarnesyl triethylsilyl ether (425681-11-4) → (+)-ambrox (ent-1) + (-)-ambroxide (6790-58-5)

Conditions	Yield
Stage #1: (E,E)-homofarnesyl triethylsilyl ether With (R)-2-(o-fluorobenzyloxy)-2'-methoxy-1,1'-binaphthyl*SnCl4 In toluene at -78℃; for 72h; Stage #2: With 1H-imidazole; triethylsilyl chloride In N,N-dimethyl-formamide at 20℃; for 5h; Stage #3: With TFA*SnCl4 In toluene at -78℃; for 24h; Further stages. Title compound not separated from byproducts.;

(4aS)-1t(?)-<2-hydroxy-ethyl>-2c(?),5,5,8a-tetramethyl-(4ar,8at)-decahydro-<2t?>naphthol → (-)-ambroxide (6790-58-5) + 8β,12-epoxy-13,14,15,16-tetranorlabdane (68365-88-8)

Conditions	Yield
With naphthalene-2-sulfonate Erhitzen unter vermindertem Druck;

8-hydroxy-15,16-dinor-labdan-13-one (16736-51-9) → (-)-ambroxide (6790-58-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 83 percent / sodium chromate; acetic anhydride; glacial acetic acid / benzene / 4 h / 70 °C 2: 95 percent / potassium borohydride / ethanol / 10 h / Heating 3: 92 percent / bromotrichloromethane; triphenylphosphine; NaHCO3 / CH2Cl2 / 6 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 83 percent / sodium chromate; acetic anhydride; glacial acetic acid / benzene / 4 h / 70 °C 2: 85 percent / zinc iodide; sodium borohydride / tetrahydrofuran / 1 h / Heating View Scheme

Farnesal (502-67-0) → (-)-ambroxide (6790-58-5)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: 96 percent / PhLi / tetrahydrofuran; cyclohexane; diethyl ether / 1 h / 20 °C 2.1: tetrahydrofuran / 24 h / 20 °C 3.1: H2O2; NaOH / tetrahydrofuran 4.1: 100 percent / imidazole / dimethylformamide / 20 °C 5.1: (R)-2-(o-fluorobenzyloxy)-2'-methoxy-1,1'-binaphthyl*SnCl4 / toluene / 72 h / -78 °C 5.2: ClSiEt3; imidazole / dimethylformamide / 5 h / 20 °C 5.3: TFA*SnCl4 / various solvent(s); toluene / 24 h / -78 °C View Scheme

2-((trifluoromethyl)thio)isoindoline-1,3-dione (719-98-2) + (-)-ambroxide (6790-58-5) → (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2-((trifluoromethyl)thio)dodecahydronaphtho[2,1-b]furan

Conditions	Yield
With sodium benzoate; [Ir(2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine)2(4,4'-di-tert-butyl-2,2'-bipyridine)](PF6) In acetonitrile at 20℃; for 2h; Inert atmosphere; Irradiation; regioselective reaction;	95%

(-)-ambroxide (6790-58-5) → (3aR)-(+)-sclareolide (564-20-5, 1216-84-8, 30450-17-0, 58976-28-6, 64090-92-2, 67844-42-2, 79768-41-5, 79768-42-6, 86688-27-9, 86688-28-0, 95406-08-9, 98719-44-9, 98719-46-1, 131831-65-7, 140851-80-5)

Conditions	Yield
With dipotassium hydrogenphosphate; C17H18ClFeN6O6(2-); 3-chloro-benzenecarboperoxoic acid In water; acetonitrile at 20℃;	90%
With (R,R)-Fe(PDP); dihydrogen peroxide; acetic acid regioselective reaction;	80%
With 2,6-dichloropyridine N-oxide; dichloro(5,10,15,20-tetramesitylporphyrinato)ruthenium(IV) In 1,2-dichloro-ethane at 40℃; for 24h; Reagent/catalyst; Inert atmosphere; regioselective reaction;	80%

P-toluenesulfonyl cyanide (19158-51-1) + (-)-ambroxide (6790-58-5) → ambroxide-12-carbonitrile (1338695-87-6)

Conditions	Yield
With benzophenone In acetonitrile at 20℃; for 2h; Inert atmosphere; UV-irradiation; stereoselective reaction;	89%
With benzophenone In acetonitrile at 20℃; for 2h; Inert atmosphere; UV-irradiation; chemoselective reaction;	89%

1,1-bis(phenylsulfonyl)ethylene (39082-53-6) + (-)-ambroxide (6790-58-5) → C30H40O5S2

Conditions	Yield
With [Ir(dF(CF3)ppy)2(5,5'dCF3bpy)]PF6; dibutylphosphoric acid tetrabutylammonium salt In dichloromethane at 20℃; for 24h; Glovebox; Inert atmosphere; Irradiation;	88%
With 2-chloroanthracene-9,10-dione In dichloromethane at 20℃; for 4h; Irradiation; Optical yield = 48 %de; diastereoselective reaction;

(-)-ambroxide (6790-58-5) → C16H27N3O

Conditions	Yield
With 4-toluenesulfonyl azide; 4-Benzoylpyridine In benzene at 20℃; for 3h; UV-irradiation; Inert atmosphere; chemoselective reaction;	77%

(prop-2-ene-1,2-diyldisulfonyl)dibenzene (2525-55-5) + (-)-ambroxide (6790-58-5) → C25H36O3S

Conditions	Yield
With pentacene-5,7,12,14-tetraone; potassium carbonate In dichloromethane at 20℃; for 24h; Inert atmosphere; Irradiation;	74%

(-)-ambroxide (6790-58-5) → (1S,6S)-2-(2-bromoethyl)-1,3,7,7-tetramethylbicyclo[4.4.0]dec-2-ene (308255-94-9)

Conditions	Yield
With boron trifluoride diethyl etherate; tetraethylammonium bromide In dichloromethane at 20℃; Ring cleavage;	72%

(4-methoxy)benzenesulfonylmethanal O-benzyl oxime + (-)-ambroxide (6790-58-5) → C24H35NO2

Conditions	Yield
With 4-Benzoylpyridine In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; UV-irradiation;	70%

(-)-ambroxide (6790-58-5) → (4aS,8aS)-5-(2-iodoethyl)-1,1,4a,6-tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene (308255-96-1)

Conditions	Yield
With aluminium trichloride; sodium iodide In dichloromethane; acetonitrile at 20℃; Ring cleavage;	69%

4-methoxycarbonylphenyl bromide (619-42-1) + (-)-ambroxide (6790-58-5) → methyl 4-((2R,3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-yl)benzoate + methyl 4-((2S,3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-yl)benzoate

Conditions	Yield
With bis(acetylacetonate)nickel(II); 5,5'-dimethyl-2,2'-bipyridine; (4-methoxyphenyl)(4-(trifluoromethyl)phenyl)methanone; sodium carbonate In benzene at 20℃; for 96h; Schlenk technique; diastereoselective reaction;	A 69% B n/a
With bis(acetylacetonate)nickel(II); 5,5'-dimethyl-2,2'-bipyridine; (4-methoxyphenyl)(4-(trifluoromethyl)phenyl)methanone; sodium hydrogencarbonate In benzene at 20℃; for 96h; Schlenk technique; Inert atmosphere; Irradiation; Overall yield = 69 %; Overall yield = 76.7 mg; diastereoselective reaction;	A n/a B n/a

Benzylidenemalononitrile (2700-22-3) + (-)-ambroxide (6790-58-5) → 2-(phenyl((3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-yl)methyl)malononitrile

Conditions	Yield
With eosin In tert-butyl alcohol at 0 - 60℃; for 48h; Sealed tube; Inert atmosphere; Irradiation;	68%

(-)-ambroxide (6790-58-5) → C16H28O3 (1217488-90-8)

Conditions	Yield
With Botrytis cynerea for 72h; Microbiological reaction; chemoselective reaction;	60%

(-)-ambroxide (6790-58-5) → (1R,2R,4aS,8aS)-(2-hydroxy-2,5,5,8a-tetramethylperhydronaphthyl)acetic acid (13456-36-5) + (3aR)-(+)-sclareolide (564-20-5, 1216-84-8, 30450-17-0, 58976-28-6, 64090-92-2, 67844-42-2, 79768-41-5, 79768-42-6, 86688-27-9, 86688-28-0, 95406-08-9, 98719-44-9, 98719-46-1, 131831-65-7, 140851-80-5)

Conditions	Yield
With [((S,S)-N,N′-bis(2-pyridylmethyl)-(S,S)-2,2′-bipyrrolidine)FeII(OTf)2]; dihydrogen peroxide; acetic acid In water; acetonitrile at 0 - 20℃; Catalytic behavior; Inert atmosphere; regiospecific reaction;	A 29% B 54%

isoquinoline (119-65-3) + (-)-ambroxide (6790-58-5) → 1-((3aR,5aS,9aS,9bR)-3 a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-yl)isoquinoline

Conditions	Yield
With ethanol; bis-[(trifluoroacetoxy)iodo]benzene In dimethyl sulfoxide; 1,2-dichloro-ethane at 20℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation; diastereoselective reaction;	53%

Upstream product

• 38419-75-9 (1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol 
• 113327-33-6 C₂₀H₃₉N₂O₃P 
• 113105-33-2 (1R,2R,4aS,8aS)-1-(2-Chloro-ethyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol 
• 105735-95-3 (1R,2R,4aS,8aS)-1-(3-Hydroperoxy-3-methyl-pent-4-enyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol 
• 31207-73-5 2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6, 7,8,8a-octahydronaphthalen-1-yl)ethan-1-ol 
• 158577-90-3 <1S-(1α,2β,3β,4β,4aβ,8aα)> decahydro-3-hydroxyl-2,5,5,8a-tetramethylnaphthalene-1-ethanol 
• 564-20-5 (3aR)-(+)-sclareolide 
• 320756-17-0 biscyclohomofarnesane-8α,12-diol 
• 10207-83-7 (8α-Methyl)-iresan-8β,11-diol 
• 145511-19-9 (+)-(1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-(3-methyl-2-butenyl)-decahydro-2-naphthalenol 
• 360048-92-6 (+)-(1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-(3-methyl-3-butenyl)-decahydro-2-naphthalenol 
• 145511-17-7 (-)-(1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-(3-methyl-3-butenyl)-decahydro-2-naphthalenyl acetate 
• 196805-72-8 2,3,4,4a,5,6,7,8-octahydro-2β,3α-dihydroxy-4aβ,8,8-trimethylnaphthalene 
• 196805-70-6 2,3,4,4a,5,6,7,8-octahydro-2β,3β-dihydroxy-4aβ,8,8-trimethylnaphthalene 

Downstream Products

• 564-20-5 (3aR)-(+)-sclareolide 
• 29064-99-1 2-oxosclareolide 
• 292643-80-2 (+)-1-oxo-sclareolide 
• 74483-92-4 (+)-3-oxo-sclareolide 
• 13456-36-5 (1R,2R,4aS,8aS)-(2-hydroxy-2,5,5,8a-tetramethylperhydronaphthyl)acetic acid 
• 1422446-22-7 C₁₆H₂₆O₃ 
• 3738-00-9 (3aRS,5aSR,9aRS,9bSR)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan 

Relevant academic research and scientific papers

Preparation of two diastereoisomeric decalin synthons and (-)-ambrox

Two diastereoisomeric decalins, (2S,4aS,5S,6R)- and (2S,4aS,5R,6R)-5-(2- hydroxyethyl)-1,1,4a,6-tetramethyldecalin-2,6-diol (5 and 6) were prepared from the degradation products of oleanolic acid. Starting from 6, (-)-ambrox (4) was synthesized.

Manganese-Catalyzed Hydrogenation of Sclareolide to Ambradiol

The hydrogenation of (+)-Sclareolide to (?)-ambradiol catalyzed by a manganese pincer complex is reported. The hydrogenation reaction is performed with an air- and moisture-stable manganese catalyst and proceeds under relatively mild reaction conditions at low manganese and base loadings. A range of other esters could be successfully hydrogenated leading to the corresponding alcohols in good to quantitative yields using this easy-to-make catalyst. A scale-up experiment was performed leading to 99.3 % of the isolated yield of (?)-Ambradiol.

METHOD FOR SYNTHESISING AMBROXIDE FROM AGERATINA JOCOTEPECANA

The present invention is related to a process for obtaining the (?)-13,14,15,16-tetranor-8a,12-labdanediol compound from the Ageratina jocotepecana plant, the process comprises the steps of a) obtaining an organic concentrated extract from the Ageratina jocotepecana shoot system; b) subjecting the organic concentrated extract to column chromatography in order to elute a fraction with the (?)-13,14,15,16-tetranor-8a,12-labdanediol compound; c) separating the eluted fractions comprising the (?)-13,14,15,16-tetranor-8a,12-labdanediol compound; and d) evaporating the organic solvent to yield the (?)-13,14,15,16-tetranor-8a,12-labdanediol compound in a solid form.

A drop of the fragrant ether perfuming preparation method

The invention discloses a preparation method for ambrox and relates to the technical field of daily use chemicals. According to the preparation method disclosed by the invention, by taking cheap and easily available ferric trichloride as a catalyst, high quality ambrox is prepared by cyclodehydrating ambradiol in an organic solvent. In the reaction, ferric trichloride is taken as the catalyst, so that the reaction temperature is low and the reaction time is short. The method disclosed by the invention further has the advantages of being clean and environmental-friendly, low in cost of product, convenient in post-treatment, more suitable for industrial production and the like.

A SOLID FORM OF (-)-AMBROX FORMED BY A BIOVERVERSION OF HOMOFARNESOL IN THE PRESENCE OF A BIOCATALYST

A solid form of (-)-Ambrox formed by a bioconversion process.

Synthesis and Applications of Cyclohexenyl Halides Obtained by a Cationic Carbocyclisation Reaction

The synthesis of cyclic alkenyl halides (mainly fluorides, chlorides and bromides) from alkynol or enyne derivatives by an acid-mediated cationic cyclisation reaction is disclosed. This high-yielding, scalable and technically simple method complements and challenges conventional methodologies. This study includes the development of biomimetic cationic cyclisation reactions of polyenyne derivatives to give interesting halogen-containing polycyclic compounds. The application of this reaction in the key step of the synthesis of two terpenes, namely austrodoral and pallescensin A, and the potent odorant 9-epi-Ambrox demonstrates the potential of the reaction for natural product synthesis.

Preparation of Ambrox from Labdanes of Dysoxylum hongkongense, and the Preparation of New Diterpenoids from Dysoxylum hongkongense

The present invention discloses eight new diterpenoids, i.e. Dysongensins A to H, extracted from the leaves and twigs of Dysoxylum hongkongense, wherein AMBROX? which is applicable in the perfume industry is prepared from Dysongensin A via a series of chemical reactions, and the cytotoxicity of Dysongensins A to H against human cancer cell lines and their antiviral and anti-inflammatory activities are determined. Therefore, in the present invention, AMBROX? prepared from Dysongensin A is a new idea for application as an odorous compound in the perfume industry, and the novel diterpenoids can be prepared as a pharmaceutical compositions and/or a drug having antiviral, anti-inflammatory and/or anti-cancer activities.

METHOD FOR THE CONVERSION OF ABIENOL TO SCLAREDIOL

A method of selective conversion of Abienol, represented by formula 1, to Sclareodial, represented by formula 2 by ozonolysis and subsequent reduction. The ozonolysis is carried out at temperatures above -60 °C, preferably in nonhalogenated solvents. R is selected from H, acetals, aminals, optionally substituted alkyl groups, such as benzyl group, carboxylates such as acetates or formates, carbonates such as methyl or ethyl carbonates, carbamates, and any protecting group which can be attached to 1 and cleaved from 2, R' is selected from CH=CH2, an alkyl moiety with C2-C20, e.g. CH2-CH3, or a cycloalkyl or polycycloalkyl moiety with C3-C20, e.g. cyclopropyl, optionally alkylated, respectively, and the wavy bond is depicting an unspecified configuration of the adjacent double bond between C2 and C3.

IMPROVEMENTS IN OR RELATING TO ORGANIC COMPOUNDS

A process for the hydrogenation of a substrate comprising a carbon heteroatom double bond in the presence of a transition metal complex comprising a tridentate or bisdentate-ligand containing a nitrogen, sulphur and phosphorus atom, of which at least the N- and P- and optionally also the S-atom coordinates with the transition metal.

Synthesis method for ambroxide

The invention discloses a synthesis method for ambroxide. According to the synthesis method, sclareol is used as a raw material, and under catalysis of phosphomolybdate, ambroxide is synthesized through a one-step reaction by means of peroxide oxidization. Compared with an existing method, the synthesis method includes few process steps and is free of environment pollution.