61597-55-5

Usage

Uses

Used in Pharmaceutical Industry:
15,16-Epoxy-12R-hydroxylabda-8(17),13(16),14-triene is used as a potential therapeutic agent for its anti-inflammatory properties, which can help in managing inflammation-related conditions.
Used in Oncology Research:
In the field of oncology, 15,16-Epoxy-12R-hydroxylabda-8(17),13(16),14-triene is used as a compound with anti-tumor activity, indicating its potential in developing treatments for various types of cancer.
Used in Microbiology:
15,16-Epoxy-12R-hydroxylabda-8(17),13(16),14-triene is utilized as an anti-microbial agent, suggesting its possible application in combating microbial infections and contributing to the development of new antibiotics.
Used in Natural Product Chemistry:
Due to its complex structure and potential biological activities, 15,16-Epoxy-12R-hydroxylabda-8(17),13(16),14-triene is used as a subject of research in natural product chemistry, with the aim of understanding its properties and exploring its potential applications in drug discovery.

Upstream product

• 383159-58-8 1-(3-furyl)-2-[(1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-methylene-1-trans-naphthyl]methylketone 
• 190264-38-1 2-((1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)-N-methoxy-N-methylacetamide 
• 909794-72-5 (R)-1-(2-(triisopropylsilyloxy)furan-3-yl)-2-((1S,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)ethanol 
• 564-20-5 (3aR)-(+)-sclareolide 
• 66890-69-5 8α-hydroxy-15,16-epoxy-labda-13(16),14-dien-12-one 
• 958885-86-4 3-[(1R)-2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]-1-hydroxyethyl]-2,5-dihydrofuran-2-one 
• 22037-28-1 3-bromofurane 
• 3243-36-5 (1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthaleneacetaldehyde 
• 434284-14-7 N-methoxy-N-methyl-2-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)acetamide 

Downstream Products

• 1011287-51-6 (1-(furan-3-yl)-2-((1S,8aS)-5,5,8a-trimethyl-2-methylidenedecahydronaphthalen-1-yl)ethoxy)triisopropylsilane 

Relevant academic research and scientific papers

Synthesis of (+)-zerumin B using a regioselective singlet oxygen furan oxidation

(Chemical Equation Presented) A short and efficient synthesis of the antitumor diterpenoid (+)-zerumin B has been accomplished starting from (+)-sclareolide. At the heart of the synthetic strategy lies the regioselective formation of the α-substituted γ-hydroxybutenolide moiety of zerumin B. This was achieved by means of a [1,4] O→C triisopropylsilyl migration followed by singlet oxygen (1O2) oxidation of the resulting 2-triisopropylsilyl-3-(α-hydroxy)alkylfuran.

Synthesis of chinensines A-E

(Chemical Equation Presented) Short and efficient syntheses of coronarin E (4) and chinensines A-E (5-9) have been accomplished. The use of two different types of reaction of singlet oxygen (1O2) lies at the heart of the synthetic st

Trypanocidal labdane diterpenoids from the seeds of Aframomum aulacocarpos (Zingiberaceae)

Two novel labdane type diterpenoids, 8β(17)-epoxy-14,15,16-trihydroxylabd-12(E)-ene (aulacocarpin C) and 15,16-epoxy-14ξ,16ξ-dimethoxylabda-8(17),12-(E)-diene (aulacocarpin D) together with the known aulacocarpin A and B; 14,15-epoxy-8(17),12(E)-labdadien-16-al, coronarin E, and 15,16-epoxy-12β-hydroxy-labda-8(17)-13(16),14-triene were isolated from the seeds of Aframomum aulacocarpos. To the best of our knowledge, the last compound was isolated from a natural source for the first time. Acid hydrolysis of aulacocarpin D led to another new labdane type diterpenoid, 15,16-epoxy-12β-methoxylabda-8(17)-13(16),14-triene. The structures of all compounds were established on the basis of their spectroscopic data. These new compounds exhibit moderate trypanocidal activity.

Facile access to labdane-type diterpenes: Synthesis of coronarin C, zerumin B, labda-8(17), 13(14)-dien-15,16-olide and derivatives from (+)-manool

A practical method for the synthesis of optically active labdane-type diterpenes from (+)-manool 8, is described. We prepared the natural labdane-type diterpene 5 via key intermediate peroxide 9 and coronarin C 1, compound 8 and zerumin B 6 via a furan photosensitised oxygenation reactions.

Synthesis and stereochemistry of the antitumor diterpenoid (+)-zerumin B

Starting from commercially available (+)-sclareolide, the first synthesis of zerumin B was achieved by a concise, highly efficient pathway featuring stereoselective addition of a new silyloxyfuryltitanium reagent to an aldehyde intermediate and silyloxyfuran oxyfunctionalization as key steps. The synthesis established the relative and absolute configuration of zerumin B along with its identity with a purportedly new diterpenoid isolated from the plant Renealmia alpinia.

Synthesis of the marine furanoditerpene (-)-marginatone

A synthesis of the marine labdane furanoditerpene (-)-marginatone 1 has been accomplished by a short sequence of reactions starting from (+)-coronarin E 5. The key step is the stereocontrolled-intramolecular electrophilic cyclisation of the (+)-dihydrocoronarin E 6, to the tetracyclic marginatane skeleton 7, which is subsequently functionalized by allylic oxidation to give 1. As (+)-coronarin E 5 was previously synthesized from (-)-sclareol 10, the herein reported preparation constitutes the first formal total synthesis of (-)-marginatone 1, by which its absolute configuration has been confirmed.