469-61-4

Basic information

• Product Name: (-)-ALPHA-CEDRENE
• Synonyms: 3abeta,7beta,8aalpha)]-3alph;7-methanoazulene,2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-,(3r-(3-alpha,3a-beta,7-beta,8a-alpha))1h-3;7-Methanoazulene,2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-,[3R-(3.alpha.,3a.beta.,7.beta.1H-3a;7-methanoazulene,2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1h-3(3r-(3-alp;7-methanoazulene,2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1h-3[3theta-(;Cedr-8-ene;levo-alpha-cedrene;(1S,2R,5S)-2,6,6,8-TETRAMETHYLTRICYCLO[5.3.1.0(1.5)]UNDEC-8-ENE
• CAS NO: 469-61-4
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• EINECS: 207-418-4
• Product Categories: Industrial/Fine Chemicals
• Mol File: 469-61-4.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 261-262 °C(lit.)
• Flash Point: 104°C
• Appearance: /
• Density: 0.932 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0177mmHg at 25°C
• Refractive Index: n20/D 1.498
• Storage Temp.: 2-8°C
• BRN: 3196861
• CAS DataBase Reference: (-)-ALPHA-CEDRENE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-ALPHA-CEDRENE(469-61-4)
• EPA Substance Registry System: (-)-ALPHA-CEDRENE(469-61-4)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/38-50/53-50
• Safety Statements: 26-60-61-24/25-23
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 2
• RTECS: PB7725000
• Hazardous Substances Data: 469-61-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A sesquiterpene that is cedrane which has a double bond between positions 8 and 9.

InChI:InChI=1/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12+,13+,15+/m1/s1

Synthetic route

cedaranyl alcohol → alpha-cedrene (469-61-4)

Conditions	Yield
With toluene-4-sulfonic acid In acetonitrile at 50℃; for 0.5h;	96%

(+)-cedryl acetate (77-54-3) → alpha-cedrene (469-61-4)

Conditions	Yield
With tetrafluoroboric acid In 1,4-dioxane at 100℃; for 1h;	93%

cedrenone (1262998-09-3) → alpha-cedrene (469-61-4)

Conditions	Yield
Stage #1: cedrenone With toluene-4-sulfonic acid hydrazide In ethanol for 2.5h; Caglioti Reductive Elimination; Reflux; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water for 2h; Reflux;	92%
With potassium hydroxide; hydrazine In diethylene glycol at 125 - 215℃; for 60h; Wolff-Kishner reduction; Inert atmosphere;	52%

(+)-cedryl acetate (77-54-3) → β‐cedrene (546-28-1) + alpha-cedrene (469-61-4)

Conditions	Yield
With acetic acid; hexacarbonyl molybdenum In tetrahydrofuran at 110℃; for 48h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With acetic acid; In 1,4-dioxane at 100℃; for 4h; Product distribution; other tertiary alcohols and acetates; various catalysts and conditions;

(+)-cedrol (77-53-2) → alpha-cedrene (469-61-4)

9α-hydroxycedrane (13567-45-8) → alpha-cedrene (469-61-4)

Conditions	Yield
With trichlorophosphate In pyridine; ethanol at 0℃; for 19h; Heating;	60 mg

carbon disulfide (75-15-0) + (+)-cedrol (77-53-2) + methyl iodide (74-88-4) → β‐cedrene (546-28-1) + alpha-cedrene (469-61-4) + Dithiocarbonic acid S-methyl ester O-((3R,3aS,6R,7R,8aS)-3,6,8,8-tetramethyl-octahydro-3a,7-methano-azulen-6-yl) ester (35812-25-0)

Conditions	Yield
Yield given. Multistep reaction;

(+)-cedrol (77-53-2) → β‐cedrene (546-28-1) + alpha-cedrene (469-61-4)

Conditions	Yield
With pyridine; trichlorophosphate In toluene for 16h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

cedrol → alpha-cedrene (469-61-4)

Conditions	Yield
With formic acid

chlorocedrene → alpha-cedrene (469-61-4)

Conditions	Yield
With ethanol; sodium

pseudocedrol → alpha-cedrene (469-61-4)

Conditions	Yield
With formic acid

(3R,3aR,6S,7S,8aS)-3,6,8,8-tetramethylhexahydro-1H-3a,7-cedaran-5(4H)-one (13794-73-5) → alpha-cedrene (469-61-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 150 mg / NaBH4 / methanol / 3 h / Ambient temperature 2: 60 mg / POCl3 / pyridine; ethanol / 19 h / 0 °C / Heating View Scheme

cedran-9-one (13567-40-3) → alpha-cedrene (469-61-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 2 g / 65 percent HClO4 / CH2Cl2 / 24 h / Ambient temperature 2: 400 mg / aq. NaHCO3 / methanol / 3 h / Heating 3: 150 mg / NaBH4 / methanol / 3 h / Ambient temperature 4: 60 mg / POCl3 / pyridine; ethanol / 19 h / 0 °C / Heating View Scheme

cedranone enol benzoate (74804-69-6, 74804-70-9) → alpha-cedrene (469-61-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 400 mg / aq. NaHCO3 / methanol / 3 h / Heating 2: 150 mg / NaBH4 / methanol / 3 h / Ambient temperature 3: 60 mg / POCl3 / pyridine; ethanol / 19 h / 0 °C / Heating View Scheme

4-desoxo-α-pipitzol benzoate (74804-66-3, 74804-67-4) → alpha-cedrene (469-61-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: Et2O*BF3 / 5 h / Ambient temperature 2: Raney Ni / ethanol / 5 h / Heating 3: 400 mg / aq. NaHCO3 / methanol / 3 h / Heating 4: 150 mg / NaBH4 / methanol / 3 h / Ambient temperature 5: 60 mg / POCl3 / pyridine; ethanol / 19 h / 0 °C / Heating View Scheme

α-pipitzol benzoate (10067-43-3, 10067-44-4) → alpha-cedrene (469-61-4)

Conditions	Yield
Multi-step reaction with 7 steps 1: 13.8 g / Et2O*BF3 / 96 h / Ambient temperature 2: W-7 Raney Ni / ethanol / 5 h / Heating 3: Et2O*BF3 / 5 h / Ambient temperature 4: Raney Ni / ethanol / 5 h / Heating 5: 400 mg / aq. NaHCO3 / methanol / 3 h / Heating 6: 150 mg / NaBH4 / methanol / 3 h / Ambient temperature 7: 60 mg / POCl3 / pyridine; ethanol / 19 h / 0 °C / Heating View Scheme

C24H30O2S2 (74804-68-5, 74842-35-6) → alpha-cedrene (469-61-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: Raney Ni / ethanol / 5 h / Heating 2: 400 mg / aq. NaHCO3 / methanol / 3 h / Heating 3: 150 mg / NaBH4 / methanol / 3 h / Ambient temperature 4: 60 mg / POCl3 / pyridine; ethanol / 19 h / 0 °C / Heating View Scheme

C24H28O3S2 (74804-65-2, 74841-96-6) → alpha-cedrene (469-61-4)

Conditions	Yield
Multi-step reaction with 6 steps 1: W-7 Raney Ni / ethanol / 5 h / Heating 2: Et2O*BF3 / 5 h / Ambient temperature 3: Raney Ni / ethanol / 5 h / Heating 4: 400 mg / aq. NaHCO3 / methanol / 3 h / Heating 5: 150 mg / NaBH4 / methanol / 3 h / Ambient temperature 6: 60 mg / POCl3 / pyridine; ethanol / 19 h / 0 °C / Heating View Scheme

tris(ammonium) (2Z,6E)-farnesyl diphosphate → (2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol (3790-71-4) + (E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol (40716-66-3) + (-)-(4S,8R)-8-epi-α-bisabolol (78148-59-1) + (-)-α-bisabolol (515-69-5, 23089-26-1, 23178-88-3, 25428-43-7, 72059-10-0, 72691-24-8, 76738-75-5, 78148-59-1, 123877-54-3) + (+)-2-epi-prezizaene (1220474-11-2) + (-)-α-acoradiene (24048-44-0) + alpha-cedrene (469-61-4) + (-)-β-curcumene (28976-67-2) + (1R,4R,5S)-1,8-dimethyl-4-(1'-methylethenyl)spiro[4.5]dec-7-ene

Conditions	Yield
With magnesium chloride In pentane at 20℃; for 19h; Inert atmosphere; Enzymatic reaction;	A 6.7 %Spectr. B 3.6 %Spectr. C 1.8 %Spectr. D 1.8 %Spectr. E 44 %Spectr. F 3.9 %Spectr. G 21.5 %Spectr. H 15.5 %Spectr. I 1.3 %Spectr.

...Expand

(2-cis,6-trans)-farnesyl diphosphate (40716-68-5) → (2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol (3790-71-4) + (E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol (40716-66-3) + (+)-2-epi-prezizaene (1220474-11-2) + (-)-α-acoradiene (24048-44-0) + epi-α-bisabolol + alpha-cedrene (469-61-4) + (-)-β-curcumene (28976-67-2) + 6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol + (1R,4R,5S)-1,8-dimethyl-4-(1'-methylethenyl)spiro[4.5]dec-7-ene

Conditions	Yield
With tobacco 5-epi-aristolochene synthase Kinetics; Enzymatic reaction;

...Expand

C12H16O2 (1262789-27-4) → alpha-cedrene (469-61-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 0.25 h / -10 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: lead(IV) tetraacetate / 2 h / 20 °C / Inert atmosphere 3.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.02 h / 20 °C / Inert atmosphere 4.1: potassium hydroxide; hydrazine / diethylene glycol / 60 h / 125 - 215 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 0.25 h / -10 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: chloroform / 2 h / -40 - 20 °C / Inert atmosphere 3.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.02 h / 20 °C / Inert atmosphere 4.1: potassium hydroxide; hydrazine / diethylene glycol / 60 h / 125 - 215 °C / Inert atmosphere View Scheme

C17H24O3 (1262789-28-5) → alpha-cedrene (469-61-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.02 h / 20 °C / Inert atmosphere 2: potassium hydroxide; hydrazine / diethylene glycol / 60 h / 125 - 215 °C / Inert atmosphere View Scheme

2-[(1R)-1,5-dimethylhex-4-enyl]-5-methylphenol (17194-58-0, 69350-75-0, 70878-71-6, 69301-27-5) → alpha-cedrene (469-61-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: lead(IV) tetraacetate / 2 h / 20 °C / Inert atmosphere 2: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.02 h / 20 °C / Inert atmosphere 3: potassium hydroxide; hydrazine / diethylene glycol / 60 h / 125 - 215 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: chloroform / 2 h / -40 - 20 °C / Inert atmosphere 2: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.02 h / 20 °C / Inert atmosphere 3: potassium hydroxide; hydrazine / diethylene glycol / 60 h / 125 - 215 °C / Inert atmosphere View Scheme

farnesyl pyrophosphate (372-97-4, 13058-04-3, 25744-33-6, 27248-37-9, 27248-38-0, 40716-68-5) → β‐cedrene (546-28-1) + (+)-cedrol (77-53-2) + alpha-cedrene (469-61-4) + (-)-(3R,3aS,6S,7R,8aS)-isocedrol (19903-73-2)

Conditions	Yield
With epicedrol synthase In aq. buffer at 30℃; for 1h; pH=8.5; Enzymatic reaction;

C15H21BrO → alpha-cedrene (469-61-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tri-n-butyl-tin hydride / pentane / 0.5 h / 0 °C 2.1: toluene-4-sulfonic acid hydrazide / ethanol / 2.5 h / Reflux 2.2: 2 h / Reflux View Scheme

(R)-2-methoxy-4-methyl-1-(6-methylhept-5-en-2-yl)benzene → alpha-cedrene (469-61-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tert-butyl methyl ether / 6 h / UV-irradiation 1.2: 0.5 h / 0 °C / Inert atmosphere 2.1: tri-n-butyl-tin hydride / pentane / 0.5 h / 0 °C 3.1: toluene-4-sulfonic acid hydrazide / ethanol / 2.5 h / Reflux 3.2: 2 h / Reflux View Scheme

alpha-cedrene (469-61-4) → (8R,9S)-cis-cedrene diol (66389-35-3)

Conditions	Yield
With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide In water; tert-butyl alcohol for 72h; Heating;	96%
Multi-step reaction with 3 steps 1.1: rose bengal; oxygen / acetonitrile / 4.5 h / 40 °C / Irradiation 1.2: 16 h / 21 °C 2.1: N,N`-sulfuryldiimidazole; dihydrogen peroxide; sodium hydroxide / water; methanol / 5 °C 3.1: lithium aluminium tetrahydride / dichloromethane / 2 h / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: rose bengal; oxygen / acetonitrile / 4.5 h / 40 °C / Irradiation 1.2: 16 h / 21 °C 2.1: dmap / dichloromethane 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 h / 21 °C 4.1: lithium aluminium tetrahydride / 2 h / 0 °C / Inert atmosphere View Scheme
With potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide In 2-methyl-propan-1-ol; water at 93 - 95℃; for 24h; Solvent;	115g

alpha-cedrene (469-61-4) → (3R,3aR,7S,8aS)-3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulen-5-amine

Conditions	Yield
With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; ammonium carbonate; 2-amino-benzenethiol In dichloromethane; acetonitrile at 20℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation;	95%
Multi-step reaction with 4 steps 1.1: dimethylsulfide borane complex / tetrahydrofuran / 4 h 1.2: 3 h 2.1: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C 3.1: sodium hydroxide; hydroxylamine hydrochloride / ethanol / 12 h / 20 °C / pH 7 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux View Scheme

alpha-cedrene (469-61-4) → (2aR,3R,5aS,7R)-3,6,6,7a-tetramethyloctahydro-2H-2a,7-cedarane[5,6-b]ethylene oxide (211379-86-1)

Conditions	Yield
With sodium percarbonate; acetic anhydride at 20℃; for 8h; Sonication;	93%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 25℃; for 8h;	83.5%
With tert.-butylhydroperoxide; di-tert-butyl peroxide In water at 69.84℃; for 8h; Reagent/catalyst;

alpha-cedrene (469-61-4) → 9β,10β-epoxy-2,2,6,10-tetramethyltricyclo[5.3.1.03,7]undecane (13567-39-0)

Conditions	Yield
With monoperoxyphthalic acid In diethyl ether at 5℃; for 96h;	89%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 0.0333333h; Inert atmosphere;

alpha-cedrene (469-61-4) + methyl 2-(4-bromophenyl)-2-diazoacetate (264881-99-4) → methyl (2R)-2-(4-bromophenyl)-3-((3R,3aS,8aS)-3,8,8-trimethyl-2,3,4,7,8,8a-hexahydro-1H-3a,7-methanoazulen-6-yl)propanoate

Conditions	Yield
With dirhodium tetrakis[(R)-(1-(biphenyl)-2,2-diphenylcyclopropanecarboxylate)] In dichloromethane at 22℃; for 3h; Inert atmosphere; Reflux; enantioselective reaction;	88%

alpha-cedrene (469-61-4) + trifluoroacetic anhydride (407-25-0) → (3R,3aR,6S,7S,8aS)-3,6,8,8-tetramethyloctahydro-1H-3a,7-cedaran-5-yl 2,2,2-trifluoroacetate

Conditions	Yield
With triethylamine In dichloromethane; water at 20℃; for 2h;	86%

alpha-cedrene (469-61-4) → 2-((2S,4R)-2-acetyl-1,1,4-trimethylhexahydropenten-3a(1H)-yl)acetic acid

Conditions	Yield
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile at 60℃; for 12h;	85%

alpha-cedrene (469-61-4) → (3R,3aR,7R,8aS)-3,6,8,8-tetramethyl-5-nitro-2,3,4,7,8,8a-hexahydro-1H-3a,7-methanoazulene

Conditions	Yield
With trifluoromethylsulfonic anhydride; tetrabutylammonium nitrate; tetrabutylammonium trifluoromethylsulfonate In dichloromethane at 30℃; for 2.5h; Inert atmosphere;	85%

alpha-cedrene (469-61-4) → (3R,3aR,6S,7S,8aS)-3,6,8,8-tetramethyloctahydro-1H-3a,7-cedaran-5-ol

Conditions	Yield
Stage #1: alpha-cedrene With dimethylsulfide borane complex In tetrahydrofuran for 4h; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran for 3h;	81%

alpha-cedrene (469-61-4) → 2-(N,N-dimethylaminomethyl)pyrrole (14745-84-7) + pyrrole (109-97-7) + N,N-dimethyl-1H-pyrrol-1-amine (78307-76-3)

Conditions	Yield
With sodium hydroxide for 24h; Heating;	A 5.5% B 41% C 53%

alpha-cedrene (469-61-4) → (3R,3aR,7S,8aS)-3,6,8,8-tetramethyl-1,2,3,7,8,8a-hexahydro-4H-3a,7-cedaran-4-one (30960-39-5)

Conditions	Yield
With pyridine; tert.-butylhydroperoxide; N-hydroxy-3,4,5,6-tetrachlorophthalimide; lithium perchlorate In acetone Electrochemical reaction; chemoselective reaction;	53%
With tert.-butylhydroperoxide; [bis(acetoxy)iodo]benzene In ethyl acetate at -20 - 20℃; for 11h;	43%

alpha-cedrene (469-61-4) → (3R,3aS,7R,8aS)-3,8,8-trimethyl-2,3,4,7,8,8a-hexahydro-1H-3a,7-cedarane-6-formaldehyde (28387-62-4) + ((3R,3aS,7R,8aS)-3,8,8-trimethyl-2,3,4,7,8,8a-hexahydro-1H-3a,7-cedaran-6-yl)methanol (21441-72-5)

Conditions	Yield
With selenium; chloroamine-T In dichloromethane at 20℃; for 36h;	A 21% B 52%

alpha-cedrene (469-61-4) → β-cedren-9-α-ol (13567-41-4) + cedr-8-en-10β-ol (1011469-40-1)

Conditions	Yield
Stage #1: alpha-cedrene With 9,10-Dicyanoanthracene; oxygen In acetonitrile for 4h; Irradiation; Stage #2: With triphenylphosphine In acetonitrile for 0.5h;	A 30% B 45%

alpha-cedrene (469-61-4) → β-cedren-9-α-ol (13567-41-4)

Conditions	Yield
Stage #1: alpha-cedrene With oxygen; rose bengal In acetonitrile at 40℃; for 4.5h; Irradiation; Stage #2: With triphenylphosphine In acetonitrile at 21℃; for 16h;	43%
Multi-step reaction with 2 steps 1: rose bengal; oxygen / acetonitrile / 4 h / Irradiation 2: triphenylphosphine / acetonitrile / 1 h View Scheme

alpha-cedrene (469-61-4) + acetic anhydride (108-24-7) → (3R-(3α,3aβ,7β,8aα))-1-(2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen-5-yl)ethan-1-one (32388-55-9) + 2,3,3,7-tetramethyl-11-methylene-12-oxatetracyclo<6.4.1.02,10.04,8>tridecane (87798-28-5) + 8-acetyl-11-hydroxy-2,6,6,7-tetramethyltricyclo<5.2.2.01,5>undecane (87798-29-6)

Conditions	Yield
With titanium tetrachloride In dichloromethane at 5℃; for 4.5h;	A 14% B 36% C 19%

N-[(1S)-amino(4-tolyl)oxido-λ4-sulfanylidene]tosylamide (816444-61-8) + alpha-cedrene (469-61-4) → (3R,3aS,7R,8aS)-[N-(S)-(p-toluenesulfonyl)-p-toluenesulfonimidoyl]-(3,8,8-trimethyl-2,3,4,7,8,8a-hexahydro-1H-3a,7-methanoazulen-6-yl)methanamine

Conditions	Yield
With Rh2(S-N-(1,8-naphthoyl)alanine)4; bis(tertbutylcarbonyloxy)iodobenzene In methanol; 1,1,2,2-tetrachloroethane at -78 - -35℃; for 72h; Molecular sieve; Inert atmosphere; regioselective reaction;	34%

alpha-cedrene (469-61-4) + ethyl (R)-2-((mesitylsulfinyl)imino)acetate → ethyl (R)-2-(((R)-mesitylsulfinyl)amino)-2-((3R,3aS,6S,7R,8aS)-3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulen-6-yl)acetate

Conditions	Yield
With phenyl[(propan-2-yl)oxy]silane; iron(III)-acetylacetonate In ethanol; 1,2-dichloro-ethane at 20℃; Inert atmosphere; diastereoselective reaction;	28%

alpha-cedrene (469-61-4) → cedr-8-en-10α-ol (18829-59-9) + cedr-8-en-10β-ol (1011469-40-1)

Conditions	Yield
With biphenyl; 9,10-Dicyanoanthracene; oxygen In acetonitrile for 20h; Irradiation;	A 15.2% B 15.2%

isocyanate de chlorosulfonyle (1189-71-5) + alpha-cedrene (469-61-4) → 2-((3R,3aS,7R,8aS)-3,8,8-Trimethyl-2,3,4,7,8,8a-hexahydro-1H-3a,7-methano-azulen-6-yl)-acetamide

Conditions	Yield
(i) CH2Cl2, (ii) aq. KOH; Multistep reaction;

alpha-cedrene (469-61-4) → (4R,6aS)-3a-Carboxymethyl-1,1,4-trimethyl-octahydro-pentalene-2-carboxylic acid

Conditions	Yield
(i) O3, CH2Cl2, (ii) aq. H2O2, (iii) Br2, NaOH; Multistep reaction;

chloro-trimethyl-silane (75-77-4) + alpha-cedrene (469-61-4) → Trimethyl-((3R,3aS,7R,8aS)-3,8,8-trimethyl-2,3,4,7,8,8a-hexahydro-1H-3a,7-methano-azulen-6-ylmethyl)-silane (105642-44-2)

Conditions	Yield
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine 1) 8 h, reflux; Yield given. Multistep reaction;

alpha-cedrene (469-61-4) → ((3R,3aS,7R,8aS)-3,8,8-trimethyl-2,3,4,7,8,8a-hexahydro-1H-3a,7-cedaran-6-yl)methanol (21441-72-5)

Conditions	Yield
With selenium(IV) oxide In ethanol for 3h; Heating; Yield given;

alpha-cedrene (469-61-4) → 8β-H-cedrane (13567-54-9)

Conditions	Yield
With hydrogen; platinum(IV) oxide In acetic acid

Upstream product

• 77-53-2 (+)-cedrol 
• 64-18-6 formic acid 
• 19903-73-2 (-)-(3R,3aS,6S,7R,8aS)-isocedrol 
• 77-53-2 α-cedrol 
• 25428-44-8 bisabolyl acetate 
• 40266-29-3 [(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl] acetate 
• 24163-97-1 (2Z,6Z)-farnesyl acetate 
• 4128-17-0 (2E,6E)-farnesyl acetate 
• 85611-33-2 (E)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate 
• 108-24-7 acetic anhydride 
• 3879-60-5 2E,6Z-farnesol 
• 16106-95-9 (2Z,6Z)-farnesol 
• 3790-71-4 (2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol 
• 24163-98-2 3,7,11-trimethyl-2E,6Z,10-dodecatrienyl ethanoate 

Downstream Products

• 10469-60-0 dihydrocedrene 
• 18829-59-9 cedr-8-en-10α-ol 
• 91-20-3 naphthalene 
• 71-43-2 benzene 
• 30960-39-5 (3R,3aR,7S,8aS)-3,6,8,8-tetramethyl-1,2,3,7,8,8a-hexahydro-4H-3a,7-cedaran-4-one 
• 28387-62-4 (3R,3aS,7R,8aS)-3,8,8-trimethyl-2,3,4,7,8,8a-hexahydro-1H-3a,7-cedarane-6-formaldehyde 
• 21441-72-5 ((3R,3aS,7R,8aS)-3,8,8-trimethyl-2,3,4,7,8,8a-hexahydro-1H-3a,7-cedaran-6-yl)methanol 
• 13794-73-5 (3R,3aR,6S,7S,8aS)-3,6,8,8-tetramethylhexahydro-1H-3a,7-cedaran-5(4H)-one 
• 141662-60-4 8β,9β-cedrene epoxide 
• 13567-39-0 9β,10β-epoxy-2,2,6,10-tetramethyltricyclo[5.3.1.0^3,7]undecane 
• 1011469-40-1 cedr-8-en-10β-ol 
• 13567-41-4 β-cedren-9-α-ol 
• 13567-40-3 5-cedranone 
• 32388-55-9 (3R-(3α,3aβ,7β,8aα))-1-(2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen-5-yl)ethan-1-one 

Relevant articles and documents

The Wender Cedrene Synthesis Revisited: A Catalytic Enantioselective Entry to the Chiral Key Intermediate

The seminal synthesis of the sesquiterpene (±)-α-cedrene reported by Wender in 1981 offers a uniquely short and elegant access to the bridged-tricyclic target compound by exploiting an intramolecular arene-olefin photocycloaddition. However, the synthesis was performed only in the racemic series so far. This synthesis was now re-investigated and the catalytic methods for the enantioselective preparation of the chiral key intermediate were evaluated. It was found that Cu-catalyzed allylic substitution of a cinnamyl chloride with MeMgBr in the presence of a Taddol-derived chiral phosphine-phosphite ligand affords the corresponding (1-methylallyl)arene with high enantioselectivity (94% ee). Hydroboration and subsequent Suzuki coupling gave (R)-curcuphenol methyl ether from which (-)-α-cedrene was prepared along the route paved by Wender.

Cedar camphor derivative as well as preparation method and application thereof

The invention relates to the technical field of synthetic drugs, in particular to a cedar camphor derivative as well as a preparation method and an application thereof. The cedar camphor derivative isany one of compounds shown in the following structural formula, tautomers, hydrates, solvates or pharmaceutically acceptable salts thereof, and the cedar camphor derivative has a good treatment effect on viruses, especially influenza viruses, so that the application range of the cedar camphor and the derivatives thereof is expanded, and the variety of the cedar camphor derivatives is expanded.

Stereoselective quenching of cedryl carbocation in epicedrol biosynthesis

Epicedrol synthase catalyzes the cyclization of achiral diphosphate substrate, (E,E)-farnesyldiphosphate (FPP) into epicedrol. GC-MS analysis of assay extracts obtained by incubating FPP with epicedrol synthase in 21.6 at % H218O buffer showed the molecular ion of 224 for epicedrol. The labeled oxygen study presented here unambiguously demonstrates that the hydroxyl group of the epicedrol synthase enzymatic product, epicedrol, is derived from a water molecule, not from the phosphate moiety of the FPP.