5153-92-4

Upstream product

• 16736-51-9 8-hydroxy-15,16-dinor-labdan-13-one 
• 3649-91-0 8,15-dihydroxy-13E-labdane 
• 515-03-7 sclareol 
• 42569-64-2 (11E)-14,15-bisnor-8α-hydroxy-11-labden-13-one 
• 52154-07-1 8α,13β-epoxy-15-norlabdan-14-oic acid 
• 546-67-8 lead(IV) tetraacetate 
• 80098-20-0 8α-(acetyloxy)-14,15-dinorlabdan-13-one 
• 596-84-9 manoyl oxide 
• 1619-25-6 (E,Z)-Labd-13-en-8α-ol 
• 515-03-7 sclareol 
• 360048-92-6 (+)-(1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-(3-methyl-3-butenyl)-decahydro-2-naphthalenol 
• 4586-83-8 farnesyl acetone acetal 
• 911397-49-4 C₂₀H₃₄O₃ 
• 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

• 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 
• 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 
• 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 starting from labdanolic acid

Iododecarboxylation of labdanolic acid (1), followed by dehydrohalogenation led to alkenes 4 and 12. Both compounds were converted into (1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyldecahydro-2- naphthalenol (8), which was transformed via cyclization into (-)-Ambrox (9).