148717-88-8

Basic information

• Product Name: (1S,12aR)-1,12,12-trimethyl-2,3,11,12,12a,13-hexahydro-1H,6H-13a,5a-(epiminomethano)indolizino[7,6-b]carbazol-15(5H)-one
• CAS NO: 148717-88-8
• Molecular Formula: C₂₂H₂₇N₃O
• Molecular Weight: 349.4693
• Mol File: 148717-88-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 585.6°C at 760 mmHg
• Flash Point: 307.9°C
• Density: 1.29g/cm³
• Vapor Pressure: 1.07E-13mmHg at 25°C
• Refractive Index: 1.684
• CAS DataBase Reference: (1S,12aR)-1,12,12-trimethyl-2,3,11,12,12a,13-hexahydro-1H,6H-13a,5a-(epiminomethano)indolizino[7,6-b]carbazol-15(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,12aR)-1,12,12-trimethyl-2,3,11,12,12a,13-hexahydro-1H,6H-13a,5a-(epiminomethano)indolizino[7,6-b]carbazol-15(5H)-one(148717-88-8)
• EPA Substance Registry System: (1S,12aR)-1,12,12-trimethyl-2,3,11,12,12a,13-hexahydro-1H,6H-13a,5a-(epiminomethano)indolizino[7,6-b]carbazol-15(5H)-one(148717-88-8)

Safety Data

• Hazardous Substances Data: 148717-88-8(Hazardous Substances Data)

Upstream product

• 22102-56-3 3-dimethylaminomethyl-2-(1',1'-dimethylallyl)indole 
• 179686-58-9 N-[(1,1-dimethylethoxy)carbonyl]-N-(3-oxobutyl)glycine ethyl ester 
• 263025-19-0 3-hydroxy-3-methyl-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-ethyl ester 
• 411225-56-4 (1S,5aR,12aR,13aS)-2,3,11,12,12a,13-hexahydro-1,12,12-trimethyl-5H,6H-5a,13a-(iminomethano)-1H-indolizino[7,6-b]carbazole-5,14-dione 
• 263025-20-3 1-[N-[(1,1-dimethylethoxy)carbonyl]-2-(1,1-dimethyl-2-propenyl)-D,L-tryptophyl]-3-hydroxy-3-methyl-D,L-proline ethyl ester 
• 263025-16-7 N-(diphenylmethylene)-2-(1,1-dimethyl-2-propenyl)-D,L-tryptophan ethyl ester 
• 263025-21-4 3-[[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]methyl]hexahydro-8-hydroxy-8-methylpyrrolo[1,2-a]pyrazine-1,4-dione 
• 263025-23-6 (3R,S)-3-[[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]methyl]-6,7-dihydro-1-methoxy-8-methylpyrrolo[1,2-a]pyrazin4(3H)-one 
• 263025-22-5 (3R,S)-3-[[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]methyl]-2,3,6,7-tetrahydro-8-methylpyrrolo[1,2-a]pyrazine-1,4-dione 
• 263025-39-4 N[(1,1-dimethylethoxy)carbonyl]-2-(1,1-dimethyl-2-propenyl)-D,L-tryptophan ethyl ester 
• 263025-18-9 N[(1,1-dimethylethoxy)carbonyl]-2-(1,1-dimethyl-2-propenyl)-D,L-tryptophan 
• 263025-17-8 2-(1,1-dimethyl-2-propenyl)-D,L-tryptophan ethyl ester 
• 129228-72-4 (3-oxo-butylamino)-acetic acid ethyl ester 
• 263025-37-2 β-hydroxy-β-methylproline ethyl ester 

Relevant articles and documents

A unified strategy to reverse-prenylated indole alkaloids: Total syntheses of preparaherquamide, premalbrancheamide, and (+)-VM-55599

A full account of our studies toward reverse-prenylated indole alkaloids that contain a bicyclo[2.2.2]core is described. A divergent route is reported which has resulted in the synthesis of preparaherquamide, (+)-VM-55599, and premalbrancheamide. An intramolecular Dieckmann cyclization between an enolate and isocyanate was used to forge the bicyclo[2.2.2]diazaoctane core that is characteristic of these molecules. The pentacyclic indole scaffold was constructed through a one-pot Hofmann rearrangement followed by Fischer indole synthesis. The utilization of our previously reported indole peripheral functionalization strategy also led to natural products including malbrancheamides B, C, stephacidin A, notoamides F, I and R, aspergamide B, and waikialoid A. Ultimately, the divergent route that we devised provided access to a wide range of prenylated indole alkaloids that are differently substituted on the cyclic amine core.

Total synthesis of VM55599. Utilization of an intramolecular Diels-Alder cycloaddition of potential biogenetic relevance

The total synthesis of VM55599, a natural metabolite of Penicillium sp. IMI332995, has been achieved via an intramolecular Diels-Alder cycloaddition of a reverse isoprene moiety across an azadiene system. The diastereoselectivity of the intramolecular Diels-Alder cycloaddition has biogenetic implications and is discussed in the context of the biogenetic relationship of VM55599 to the paraherquamides.