1618-78-6

Usage

Uses

Used in Pharmaceutical Industry:
(3S)-3β,5aα,9-Trimethyl-2,3,3aβ,4,5,5a,8,9bβ-octahydronaphtho[1,2-b]furan-2,8-dione is used as a potential pharmaceutical agent due to its unique molecular structure. Its specific properties may allow it to be utilized in the development of new drugs or therapeutic agents, although further research is needed to determine its exact applications and efficacy.
Used in Chemical Industry:
In the chemical industry, (3S)-3β,5aα,9-Trimethyl-2,3,3aβ,4,5,5a,8,9bβ-octahydronaphtho[1,2-b]furan-2,8-dione may serve as a key intermediate or building block in the synthesis of other complex organic compounds. Its unique structure could be leveraged to create novel chemical entities with specific functions or properties, contributing to advancements in various chemical applications.

Upstream product

• 3466-64-6 (+)-2-(1,2,3,4,4a,5,6,7-octahydro-4a,8-dimethyl-7-oxo-2-naphthyl)-propionic acid 
• 481-06-1 santonin 
• 7647-01-0 hydrogenchloride 
• 68-12-2 N,N-dimethyl-formamide 
• 18409-83-1 (+/-)-Dihydro-α-santonin 
• 108-75-8 2,4,6-trimethyl-pyridine 
• 108839-76-5 (11R)-2ξ-bromo-6α-hydroxy-3-oxo-7βH-eudesm-4-en-12-oic acid-lactone 
• 108839-76-5 ent-(11R)-2ξ-bromo-6β-hydroxy-3-oxo-eudesm-4-en-12-oic acid-lactone 
• 108839-76-5 rac-(11S)-2ξ-bromo-6β-hydroxy-3-oxo-eudesm-4-en-12-oic acid-lactone 
• 104-90-5 5-ethyl-2-methyl-pyridine 
• 481-06-1 α-Santonin 
• 101887-02-9 rac-(11R)-3-acetoxy-eudesma-3,5-dien-12-oic acid methyl ester 
• 101887-02-9 rac-(11S)-3-acetoxy-eudesma-3,5-dien-12-oic acid methyl ester 
• 18409-83-1 (+/-)-Dihydrosantonin-C 

Downstream Products

• 13743-88-9 (-)-α-desmotroposantonin 
• 135441-96-2 2-((2R,4aR,5S)-4a,8-Dimethyl-7-oxo-5-phenylselanyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-2-yl)-propionic acid methyl ester 
• 16963-59-0 (+)-α-Desmotroposantonin 
• 13743-96-9 (+)-β-desmotroposantonin 
• 79-59-4 rac-(11R)-6β-hydroxy-3-oxo-eudesma-1,4-dien-12-oic acid 
• 79-59-4 rac-(11S)-6α-hydroxy-3-oxo-eudesma-1,4-dien-12-oic acid 
• 481-06-1 (+/-)-Santonin-C 
• 438-50-6 (+/-)-α-Desmotroposantonin 
• 481-06-1 (+/-)-Santonin-D 
• 473-08-5 eudesma-4,11-dien-3-one 
• 10208-54-5 chamaecynone 
• 10208-55-6 isochamaecynone 
• 132185-40-1 4-epi-6β-vulgarin 
• 132185-41-2 6β-vulgarin 

Relevant academic research and scientific papers

Synthesis of 6-epi-tuberiferin and the biological activities of tuberiferin, dehydrobrabrachylaenolide, 6-epi-tuberiferin, and their synthetic intermediates

Tuberiferin, 6-epi-tuberifelin, dehydrobrachylaenolide and two series of eudesmanolides, eudesmane-12,6 α-lactones and eudesmane-12,6β-lactones, were synthesized for the studies of the structure–activity relationships to explore novel anti-inflammatory, a

Synthetic approach to exo-endo cross-conjugated cyclohexadienones and its application to the syntheses of dehydrobrachylaenolide, isodehydrochamaecynone, and trans-isodehydrochamaecynone

Methodology for synthesis of exo-endo cross-conjugated dienones with trans- and cis-decalin systems has been reported. Bromination of the silyl enol ether of α′-methyl α,β-unsaturated ketones with PTAB and successive dehydrobromination of the resulting α′-bromo-α′-methyl α,β-unsaturated ketones under three conditions (DBU/PhH; TBAF/THF; Li2CO3, LiBr/DMF) gave the desired exo-endo cross-conjugated dienones in good yield. This method was applied to the syntheses of dehydrobrachylaenolide (1), isodehydro-chamaecynone (5c), and trans-isodehydrochamaecynone (11) starting from tuberiferine (7), chamaecynone (5a), and trans-chamaecynone (9). Eudesmanolides possessing an α-methylene γ-lactone moiety, i.e., 1, 7, and 13, exhibited significant inhibitory activity toward the induction of the intercellular adhesion molecule-1 (ICAM-1). Compound 1 showed greater activity than 7 and 13. All compounds possessing an ethynyl group, 5d, 9, 11, and 14, showed the same degree of termiticidal activity, and the exo-endo cross-conjugated dienone structure in 11 had no influence on the activity.

SYNTHESIS, BIOTRANSFORMATION AND STEREOCHEMISTRY OF 6β-SESQUITERPENE LACTONES: SYNTHESES OF 6β-ARTEPAULIN, 11,13-DIHYDRO-6β-TUBERIFERIN, 5,15-DIHYDRO-6β-OOPODIN, 4-EPI-6β-VULGARIN AND 6β-VULGARIN

6β-Artepaulin, 11,13-dihydro-6β-tuberiferin, 4,15-dihydro-6β-oopodin, 4-epi-6β-vulgarin and 6β-vulgarin were obtained from α-santonin.Stereochemical studies showed that the configuration at C-6 is decisive in the chemical behaviour of the A ring.Biotransformation of 1-oxo-5,6α,4,11βH-eudesm-2-en-6,12-olide with Rhizopus nigricans cultures probed to be a very efficient alternative way to obtain 4-epi-6β-vulgarin, which was then converted to 6β-vulgarin, a convenient starting material for biogenetical studies of pseudoguaianolides.A new 8β-hydroxyl derivative obtained from this biotransformation constitutes a new approach to the synthesis of 8,12-eudesmanolides and other sesquiterpenolides.Molecular structures were determined mainly by mono- and bidimensional nmr experiments.

THE TOTAL SYNTHESIS OF 1-OXYGENATED EUDESMANOLIDES

A route towards 1-oxygenated eudesmanolides, via a (2+2) photocycloaddition reaction for constructing the decalin framework is described.The following natural substances have been synthesized. (+/-)-dihydroreynosin (1), (+/-)-1-oxo-dihydromagnolialide (2)