5153-92-4

Upstream product

• 16736-51-9 8-hydroxy-15,16-dinor-labdan-13-one 
• 42569-64-2 (11E)-14,15-bisnor-8α-hydroxy-11-labden-13-one 
• 80098-20-0 8α-(acetyloxy)-14,15-dinorlabdan-13-one 
• 515-03-7 sclareol 
• 1619-25-6 (E,Z)-Labd-13-en-8α-ol 
• 515-03-7 sclareol 
• 119987-19-8 isosclareyl diacetate 
• 1117-52-8 6,10,14-trimethyl-5,9,13-pentadecatriene-2-on 
• 3649-91-0 8,15-dihydroxy-13E-labdane 
• 596-84-9 manoyl oxide 
• 52154-07-1 8α,13β-epoxy-15-norlabdan-14-oic acid 
• 546-67-8 lead(IV) tetraacetate 
• 25578-83-0 Neoabienol 
• 67987-70-6 2-methyl-2-(2-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydronaphthalen-1-yl)ethyl)-1,3-dioxolane 

Downstream Products

• 67779-53-7 (-)-pumiloxide 
• 13456-36-5 (1R,2R,4aS,8aS)-(2-hydroxy-2,5,5,8a-tetramethylperhydronaphthyl)acetic acid 
• 564-20-5 (3aR)-(+)-sclareolide 
• 38419-77-1 (4aS,6aR,11aR,11bS)-4,4,6a,11b-Tetramethyl-dodecahydro-7,9-dioxa-cyclohepta[a]naphthalene 
• 178394-54-2 C₂₃H₃₄O₂ 
• 150267-50-8 (4aS,5S,8aS)-5-(2-Benzyloxy-ethyl)-1,1,4a-trimethyl-6-methylene-decahydro-naphthalene 
• 150267-49-5 (1R,2R,4aS,8aS)-1-(2-(benzyloxy)ethyl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol 
• 6790-58-5 (-)-ambroxide 
• 597541-58-7 Toluene-4-sulfonic acid (2S,3S)-3-methyl-3-[2-(3,4,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl]-oxiranylmethyl ester 
• 103476-92-2 (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-ol 

Relevant academic research and scientific papers

Scalable synthesis of methyl ent-isocopalate and its derivatives

An efficient and convenient synthetic route was developed to prepare the tricycle diterpene intermediates 1-3 starting from commercially available (-)-sclareol. This improved approach involving four-step reactions provides large-scale (30-40 g) methyl ent-isocopalate in 61% overall yield, which could supply sufficient material for the synthesis of marine natural products containing tricyclic diterpenes.

Synthesis of 13-amino-14,15-dinorlabd-8(9)-ene from sclareol

13-Amino-14,15-dinorlabd-8(9)-ene was synthesized from sclareol in four steps in 47% total yield. 14,15-Dinorlabd-8(9)-en-13-one was an intermediate compound, reduction of its oxime with LiAlH4 was a key step of this synthetic scheme.

Catalytic epoxypolyene cyclization via radicals: A simple total synthesis of sclareol oxide and its 8-epimer

A short synthesis of sclareol oxide from epoxyfarnesyl acetone in six steps is described. The strategy features a titanocene-catalyzed epoxypolyene cyclization for the construction of the carbocyclic core structure. The exo olefin formed during the termin

Process for the preparation of ketones by ozonolysis

The invention relates to a process for the preparation of a ketone from a tertiary alcohol having a double bond in the alpha position, that includes the step of contacting tertiary alcohol having a double bond in the alpha position with ozone in the presence of an inorganic base under ketone-forming reaction conditions.

Synthesis of (+)-drim-9(11)-en-8α-ol from sclareol

A drimane-type sesquiterpenoid, (+)-drim-9(11)-en-8α-ol, was synthesized from sclareol in four steps. The ozonolysis product of sclareol diacetate reacts with Cu(OAc)2·H2O to give 8α-acetoxy-14,15-bisnorlabdan-13-one. Photolysis of this compound followed by alkaline hydrolysis results in the target compound belonging to the normal steric series. (+)-Drim-9(11)-en-8α-ol acetate is highly unstable and decomposes during chromatography on SiO2.

An improved synthesis of rhinocerotinoic acid

The stereoselective synthesis of E-rhinocerotinoic acid has been achieved in five steps from (-)-sclareol in an overall yield of 32%. This constitutes a significant improvement on the previous synthesis of this anti-inflammatory compound.

Synthesis and absolute configuration of (-)-chrysolic acid and (+)-isofregenedol

An efficient synthesis of (-)-chrysolic acid and (+)-isofregenedol has been achieved from zamoranic acid and sclareol. The characteristic tetrahydronaphtalenic system was obtained by use of a cationic rearrangement of bicyclic systems adequately functionalized. The absolute configuration of the natural products was established using Sharpless asymmetric epoxidation.

Synthesis of Ambrox from labdanolic acid

A synthesis of the valuable amber-type odorant Ambrox from labdanolic acid (main diterpenoid of the acid fraction of non-polar extracts of Cistus ladaniferus L.) is reported. The conversion is based on (a) the α,β-dehydrogenation of methyl labdanolate using an organoselenium reagent, (b) subsequent oxidative degradations of the side chain, and (c) final acid-promoted cyclization of the resulting tetranorlabdan-8α,12-diol. The influence of the temperature and solvent in the cyclization of the diol with p-toluenesulfonic acid is also described. Thus, Ambrox has been obtained by a six-step procedure in 33% overall yield from methyl labdanolate.

The synthesis of Ambrox-like compounds starting from (+)-larixol

The oxidation of the (3-hydroxy-3-methyl-4-pentenyl)-side chain at C(9) of some labdanic diterpenoids with potassium permanganate was investigated. Triols, ketones, or cyclic enol ethers are the main reaction products, strongly influenced by the substituent at C(8). Further degradation of the methyl ketones by the Baeyer-Villiger reaction and modification of the exocyclic 8(17) double bond lead to suitable intermediates, which have been transformed into Ambrox-like compounds. Synthetic routes using palladium catalyzed elimination or isomerization of allylic acetates, followed by ozonolysis have been developed as well for shortening of the side chain of (+)-larixol. Products from both routes have been cyclized to 6α-hydroxy Ambrox. This compound was used as the key intermediate for the synthesis of several other Ambrox-like compounds of which some showed pleasant odour properties.