1438-57-9

Usage

Uses

Used in Pharmaceutical Applications:
(2R,5S)-4,4'aα,5,5',6',7',8',8'a-Octahydro-2',5,5',5',8'aβ-pentamethylspiro[furan-2(3H),1'(4'H)-naphthalene]-5-acetic acid is used as a potential pharmaceutical agent for its Nox4 inhibition and antitumor activity. The compound's unique structure and stereochemistry may contribute to its ability to modulate specific biological pathways, making it a promising candidate for the development of new drugs targeting cancer and other diseases.
Used in Drug Delivery Systems:
In the field of drug delivery, (2R,5S)-4,4'aα,5,5',6',7',8',8'a-Octahydro-2',5,5',5',8'aβ-pentamethylspiro[furan-2(3H),1'(4'H)-naphthalene]-5-acetic acid may be utilized as a component in the design of novel drug delivery systems. Its chemical properties, such as the carboxylic acid group, could be exploited for conjugation to various carriers, enhancing the compound's delivery, bioavailability, and therapeutic outcomes.
Used in Chemical Synthesis:
(2R,5S)-4,4'aα,5,5',6',7',8',8'a-Octahydro-2',5,5',5',8'aβ-pentamethylspiro[furan-2(3H),1'(4'H)-naphthalene]-5-acetic acid may also find applications in chemical synthesis, serving as a building block or intermediate for the synthesis of more complex molecules with diverse biological activities. Its unique structure and functional groups could be valuable in the development of new compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 1438-58-0 grindelic acid methyl ester 

Downstream Products

• 102505-47-5 (S)-3-Hydroxy-3-methyl-5-((4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pentanoic acid methyl ester 
• 1438-58-0 grindelic acid methyl ester 
• 125404-46-8 (S)-3-Hydroxy-3-methyl-6-oxo-6-[(1S,2S)-1,3,3-trimethyl-2-(3-oxo-butyl)-cyclohexyl]-hexanoic acid methyl ester 
• 1438-58-0 methyl grindelate 
• 102505-47-5 (S)-3-Hydroxy-3-methyl-5-((S)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pentanoic acid methyl ester 
• 1456515-59-5 C₃₇H₅₀N₂O₃ 
• 1456515-58-4 N-butyl-2-methyl-2-(2-((1'R,5S,8a'S)-2',5,5',5',8a'-pentamethyl-4,4a',5,5',6',7',8',8a'-octahydro-3H,4'H-spiro[furan-2,1'-naphthalene]-5-yl)-N-phenylacetamido)propanamide 
• 1456515-57-3 N-(2,6-dimethylphenyl)-2-methyl-2-(2-((1'R,5S,8a'S)-2',5,5',5',8a'-pentamethyl-4,4a',5,5',6',7',8',8a'-octahydro-3H,4'H-spiro[furan-2,1'-naphthalene]-5-yl)-N-phenylacetamido)propanamide 
• 1456515-60-8 N-cyclohexyl-2-methyl-2-(2-((1'R,5S,8a'S)-2',5,5',5',8a'-pentamethyl-4,4a',5,5',6',7',8',8a'-octahydro-3H,4'H-spiro[furan-2,1'-naphthalene]-5-yl)-N-phenylacetamido)propanamide 
• 1456515-56-2 N-tert-butyl-2-methyl-2-(2-((1'R,4a'S,5S,8a'S)-2',5,5',5',8a'-pentamethyl-4,4a',5,5',6',7',8',8a'-octahydro-3H,4'H-spiro[furan-2,1'-naphthalene]-5-yl)-N-phenylacetamido)propanamide 
• 1456515-54-0 2-(N-benzyl-2-((1'R,5S,8a'S)-2',5,5',5',8a'-pentamethyl-4,4a',5,5',6',7',8',8a'-octahydro-3H,4'H-spiro[furan-2,1'-naphthalene]-5-yl)acetamido)-2-methyl-N-(2-morpholinoethyl)propanamide 
• 1456515-53-9 2-(N-benzyl-2-((1'R,5S,8a'S)-2',5,5',5',8a'-pentamethyl-4,4a',5,5',6',7',8',8a'-octahydro-3H,4'H-spiro[furan-2,1'-naphthalene]-5-yl)acetamido)-N-butyl-2-methylpropanamide 
• 1456515-52-8 2-(N-benzyl-2-((1'R,5S,8a'S)-2',5,5',5',8a'-pentamethyl-4,4a',5,5',6',7',8',8a'-octahydro-3H,4'H-spiro[furan-2,1'-naphthalene]-5-yl)acetamido)-N-(2,6-dimethylphenyl)-2-methylpropanamide 
• 1456515-51-7 2-(N-benzyl-2-((1'R,5S,8a'S)-2',5,5',5',8a'-pentamethyl-4,4a',5,5',6',7',8',8a'-octahydro-3H,4'H-spiro[furan-2,1'-naphthalene]-5-yl)acetamido)-N-cyclohexyl-2-methylpropanamide 

Relevant academic research and scientific papers

Stereocontrolled synthesis of ent-grindelic acid. A useful example of diastereofacial guidance in an oxonium ion-initiated pinacolic ring expansion

An enantioselective synthesis of (+)-grindelic acid is described, confirming that the dextrorotatory enantiomer is antipodal to the natural diterpenoid. The optically pure bicyclic ketone 5 representing the AB ring system is constructed from the levorotatory Wieland-Miescher ketone and must therefore possess the absolute configuration shown. Coupling of 5 with the 5-lithio derivative of optically active 2,3-dihydrofuran 3 derived from (R)-(-)-linalool was effected for the purpose of realizing acid-catalyzed rearrangement with generation of the appropriate spirocyclic framework. This key step is highly stereocontrolled, leading predominantly to 7. Once the advanced intermediate 15 is available in this fashion, its subsequent exposure to oxidation and dehydration steps led to the target molecule. The synthesis demonstrates unequivocally that natural (-)-grindelic acid is a true labdane diterpenoid.