794528-61-3

Basic information

• Product Name: 2H-Furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione,octahydro-1-methyl-,(1R,3aR,10aS,10bS)-(9CI)
• Synonyms: 2H-Furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione,octahydro-1-methyl-,(1R,3aR,10aS,10bS)-(9CI)
• CAS NO: 794528-61-3
• Molecular Formula: C12H17NO3
• Molecular Weight: 0
• Product Categories: METHYL
• Mol File: 794528-61-3.mol
• Article Data: 27

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2H-Furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione,octahydro-1-methyl-,(1R,3aR,10aS,10bS)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione,octahydro-1-methyl-,(1R,3aR,10aS,10bS)-(9CI)(794528-61-3)
• EPA Substance Registry System: 2H-Furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione,octahydro-1-methyl-,(1R,3aR,10aS,10bS)-(9CI)(794528-61-3)

Safety Data

• Hazardous Substances Data: 794528-61-3(Hazardous Substances Data)

Upstream product

• 885971-45-9 3a,6,8,9,9a,9b-hexahydro-1H-3-oxa-6a-aza-cyclopenta[e]azulene-2,7-dione 
• 885971-59-5 5-acetoxy N-crotyl pyyrolidine-2-one 
• 736142-12-4 (3aS,10aS)-3a,4,5,6,10,10a-hexahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(9H)dione 
• 183994-53-8 (S)-5-ethynyl-1-(pent-4-enyl)pyrrolidin-2-one 
• 941676-48-8 C₁₁H₁₅NO₃ 
• 941676-29-5 C₁₃H₁₉NO₃ 
• 941676-44-4 ethyl 3-((S)-5-oxo-1-(pent-4-enyl)pyrrolidin-2-yl)but-3-enoate 
• 941676-33-1 (S)-5-(1-iodovinyl)-1-(pent-4-enyl)pyrrolidin-2-one 
• 410535-69-2 (3aR,10aS,10bR)-octahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione 
• 74-88-4 methyl iodide 
• 183994-61-8 (3aR,10aS)-1-methyl-3a,4,5,6,8,9,10,10a-octahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,8-dione 

Relevant articles and documents

Synthesis of the Proposed Structures of Parvistemoamide and Their Transformations to Stemoamide Derivatives

The proposed structures of parvistemoamide have been achieved by macrolactamization, but none of the characterization data of synthetic samples matched with those of the natural sample. The transformation of the highly strained 10-membered lactam ring in parvistemoamide into the pyrrolo[1,2-a]-azepine nucleus in stemoamide is accomplished for the first time by either transannular cyclization or Pilli's transformation. This research may promote the total synthesis of other more complex stemoamide-type or medium-sized-ring-containing Stemona alkaloids.

Total synthesis of (-)-stemoamide using ruthenium-catalyzed enyne metathesis reaction

A total synthesis of (-)-stemoamide was achieved from (-)-pyroglutamic acid using a ruthenium-catalyzed enyne metathesis as a key step, in 14 steps in 9percent overall yield.

Total synthesis of (±)-stemoamide

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Lactam Strategy Using Amide-Selective Nucleophilic Addition for Quick Access to Complex Amines: Unified Total Synthesis of Stemoamide-Type Alkaloids

Our research group has been exploring a lactam strategy for the concise total synthesis of complex alkaloids. In this article, we report full details of the unified total synthesis of stemoamide-type alkaloids by chemoselective assembly of five-membered rings based on the lactam strategy. First, the concise and gram-scale synthesis of tricyclic stemoamide was achieved by vinylogous Michael addition-reduction sequence of an unsaturated γ-lactam with an unsaturated γ-lactone, followed by N-alkylation to form the seven-membered ring. From stemoamide as a common intermediate, chemoselective nucleophilic addition of unsaturated lactone derivatives provides tetracyclic natural products. While stemonine is obtained by an Ir-catalyzed lactam-selective reductive Mannich reaction, saxorumamide and isosaxorumamide are produced through the lactone-selective nucleophilic addition of the lithiated 2- silyl furan. The developed conditions for the lactam-selective nucleophilic reactions are highly general, and were found to be applicable to the total synthesis of pentacyclic stemocochinin and isostemocochinin. The strategy enables the concise and unified total synthesis of tricyclic, tetracyclic and pentacyclic stemoamide-type alkaloids within 12 steps from a commercially available compound.