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

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

• 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 
• 500-99-2 3,5-dimethoxyphenol 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 65092-79-7 3,4-Dimethyl-2-phenyl-6-[1-phenyl-meth-(Z)-ylidene]-[1,4]oxazepane-5,7-dione 
• 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 
• 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 
• 132491-33-9 (2S,3S,3aR,8bR)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-1-oxo-3-phenyl-8b-trimethylsilanyloxy-1,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-2,2-dicarboxylic acid benzyl ester methyl 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.

Intercepted Retro-Nazarov Reaction: Syntheses of Amidino-Rocaglate Derivatives and Their Biological Evaluation as eIF4A Inhibitors

Rocaglates are a family of natural products isolated from the genus Aglaia which possess a highly substituted cyclopenta[b]benzofuran skeleton and inhibit cap-dependent protein synthesis. Rocaglates are attractive compounds due to their potential for inhibiting tumor cell maintenance in vivo by specifically targeting eukaryotic initiation factor 4A (eIF4A) and interfering with recruitment of ribosomes to mRNA. In this paper, we describe an intercepted retro-Nazarov reaction utilizing intramolecular tosyl migration to generate a reactive oxyallyl cation on the rocaglate skeleton. Trapping of the oxyallyl cation with a diverse range of nucleophiles has been used to generate over 50 novel amidino-rocaglate (ADR) and amino-rocaglate derivatives. Subsequently, these derivatives were evaluated for their ability to inhibit cap-dependent protein synthesis where they were found to outperform previous lead compounds including the rocaglate hydroxamate CR-1-31-B.

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.