1139257-91-2

Basic information

• Product Name: (2R,3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-1-oxo-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxamide
• Synonyms: (2R,3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-1-oxo-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxamide
• CAS NO: 1139257-91-2
• Molecular Weight: 503.552
• Mol File: 1139257-91-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2R,3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-1-oxo-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-1-oxo-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxamide(1139257-91-2)
• EPA Substance Registry System: (2R,3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-1-oxo-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxamide(1139257-91-2)

Safety Data

• Hazardous Substances Data: 1139257-91-2(Hazardous Substances Data)

Upstream product

• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 1098-92-6 kaempferol 5,7,4'-trimethyl ether 
• 124-40-3 dimethyl amine 
• 83768-75-6 2-hydroxy-1-(2-hydroxy-4,6-dimethoxyphenyl)ethan-1-one 
• 901774-42-3 trimethoxy cyclopenta[bc]benzopyran 
• 132491-34-0 (3aS,8bR)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-1-oxo-3-phenyl-8b-trimethylsilanyloxy-3a,8b-dihydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylic acid dimethylamide 
• 132464-01-8 (3aS,8bR)-methyl 6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-8b-((trimethylsilyl)oxy)-3a,8b-dihydro-1H-cyclopenta[b]-benzofuran-2-carboxylate 
• 65092-79-7 3,4-Dimethyl-2-phenyl-6-[1-phenyl-meth-(Z)-ylidene]-[1,4]oxazepane-5,7-dione 
• 500-99-2 3,5-dimethoxyphenol 
• 132464-03-0 (2R,3S,3aR,8bR)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-1-oxo-3-phenyl-8b-trimethylsilanyloxy-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylic acid dimethylamide 
• 52189-63-6 3,5-dimethoxyfluorobenzene 
• 132464-00-7 (2S,3R,3aR,8bR)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-1-oxo-3-phenyl-8b-trimethylsilanyloxy-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylic acid methyl ester 
• 123356-52-5 (2S,3S)-3-(4-Methoxy-phenyl)-4-oxo-2-phenyl-cyclopentane-1,1-dicarboxylic acid dimethyl ester 

Downstream Products

• 84573-16-0 rocaglamide 

Relevant articles and documents

Synthesis of each enantiomer of rocaglamide by means of a palladium(0)-catalyzed nazarov-type cyclization

A recently reported Pd0-catalyzed asymmetric Nazarov-type cyclization has been successfully applied in the key step of the first catalytic asymmetric total synthesis of (-)-rocaglamide (natural) and (+)-rocaglamide. The stereochemistry at the C3 position that controls the stereochemistry of all other stereocenters is determined in the cyclization step. This versatile and modular synthesis proceeds from simple reagents.

The Evolution of the Total Synthesis of Rocaglamide

The complex flavagline, (?)-rocaglamide, possesses a synthetically intriguing tricyclic scaffold with five contiguous stereocenters and also exhibits potent anticancer, anti-inflammatory and insecticidal activity. This full account details distinct approaches to (±)- and (?)-rocaglamide utilizing Br?nsted acid catalyzed and asymmetric Pd0-catalyzed Nazarov chemistry developed in our laboratory, respectively. The successful asymmetric synthesis revealed unforeseen mechanistic complexity that required adjusting our strategy to overcome an unanticipated racemization process, an unusual reversible ring-cleavage step and a very facile trialkylsilyl group migration.