95586-10-0

Basic information

• Product Name: (+/-)-Agroclavine I
• Synonyms: (+/-)-Agroclavine I
• CAS NO: 95586-10-0
• Molecular Weight: 238.332
• Mol File: 95586-10-0.mol

Chemical Properties

• CAS DataBase Reference: (+/-)-Agroclavine I(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-Agroclavine I(95586-10-0)
• EPA Substance Registry System: (+/-)-Agroclavine I(95586-10-0)

Safety Data

• Hazardous Substances Data: 95586-10-0(Hazardous Substances Data)

Upstream product

• 89651-12-7 (3β)-9,10-Didehydro-2,3-dihydro-1-<(4-methoxyphenyl)sulfonyl>-6-methyl-8-methyleneergoline 
• 89651-14-9 (3β)-2,3-Dihydroagroclavine I 
• 1150-43-2 (+/-)-isochanoclavine-II 
• 95484-82-5 (6aR,10aS)-7,9-Dimethyl-4,6a,7,10a-tetrahydro-6H-indolo[4,3-fg]quinolin-8-one 
• 99499-51-1 (3α,8α,9α,10α)-2,3-Dihydro-1-<(4-methoxyphenyl)sulfonyl>-6,8-dimethylergolin-9-ol 
• 101926-52-7 (3α,10α)-8,9-Didehydro-2,3-dihydro-1-<(4-methoxyphenyl)sulfonyl>-6,8-dimethylergoline 
• 89651-11-6 (3α,8α,9α,10α)-2,3-Dihydro-8-hydroxymethyl-1-<(4-methoxyphenyl)sulfonyl>-6-methylergolin-9-ol 
• 99499-50-0 Methanesulfonic acid (5aS,6aR,9R,10R,10aS)-10-hydroxy-4-(4-methoxy-benzenesulfonyl)-7-methyl-4,5,5a,6,6a,7,8,9,10,10a-decahydro-indolo[4,3-fg]quinolin-9-ylmethyl ester 
• 95484-73-4 4-((E)-2-Methoxy-vinyl)-3-(2-oxo-ethyl)-indole-1-carboxylic acid ethyl ester 
• 95484-81-4 (6aR,9R,10S,10aS)-10-Hydroxy-7,9-dimethyl-4,6a,7,9,10,10a-hexahydro-6H-indolo[4,3-fg]quinolin-8-one 
• 95484-74-5 (6aR,9S,9aS)-9-Methoxy-7-methyl-6a,7,9,9a-tetrahydro-6H-8-oxa-4,7-diaza-cyclopenta[e]acenaphthylene-4-carboxylic acid ethyl ester 
• 95484-80-3 (6aR,9R,10S,10aS)-10-Hydroxy-7,9-dimethyl-8-oxo-6a,7,8,9,10,10a-hexahydro-6H-indolo[4,3-fg]quinoline-4-carboxylic acid ethyl ester 
• 79133-62-3 (+)-4,5-cis-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole 
• 79133-62-3 4,5-trans-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenz-indole 

Relevant articles and documents

Synthetic studies directed toward ergot alkaloids, (±)-6,7-secoagroclavine, (±)-chanoclavine-1, (±)-chanoclavine-II, and (±)-agroclavine-I, by an efficient and common synthetic route

Novel three synthetic routes to (±)-6,7-secoagroclavine were developed from either methyl 3-(3-formylindol-4-yl)acrylate, indole-4-carbaldehyde, or 4-iodoindole-3-carbaldehyde. The total syntheses of (±)-chanoclavine-I, (±)-chanoclavine-II, and (±)-agroclavine-I were accomplished as well from the synthetic intermediates involved in the synthesis of (±)-6,7-secoagroclavine, culminating in establishing an efficient and common synthetic method for ergot alkaloids.

TOTAL SYNTHESES OF (+/-)-AGROCLAVINE-I, (+/-)-6-NOR-CHANOCLAVINE-II, AND (+/-)-CHANOCLAVINE-II

The first total syntheses of (+/-)-6-nor-chanoclavine-II and (+/-)-chanoclavine-II are achieved.Total synthesis of (+/-)-agroclavine-I is also reported.

SHORT-STEP SYNTHESIS OF THE ERGOT ALKALOIDS, (+/-)-NORCHANOCLAVINE-I, (+/-)-CHANOCLAVINE-I, (+/-)-ISOCHANOCLAVINE-I, and (+/-)-AGROCLAVINE

The simple total synthesis of the ergot alkaloids, (+/-)-norchanoclavine-I, (+/-)-chanoclavine-I, (+/-)-isochanoclavine-I, and (+/-)-agroclavine was achieved by a practical and common synthesis method.A new regio-selective oxidation of the Z-methyl group of the isoprenyl system with selenium dioxide is described.Keywords - (+/-)-norchanoclavine-I; (+/-)-norisochanoclavine-I; (+/-)-chanoclavine-I; (+/-)-isochanoclavine-I; (+/-)-agroclavine; ergot alkaloid; total synthesis; common synthesis method; new oxidation

A TOTAL SYNTHESIS OF (+/-)-AGROCLAVINE-I. A NEW C/D-cis-8-ERGOLENE ALKALOID

A new total synthesis of (+/-)-agroclavine-I was described

A TOTAL SYNTHESIS OF (+/-)-LYSERGENE AND (+/-)-AGROCLAVINE

A preliminary study on the exploitation of a general synthetic route to the ergoline group of alkaloids on the despyrrole analogs was succesfully extended to the first total synthesis of racemic lysergene and agroclavine via the route involving reductive photocyclization of the furylenamide (10) followed by ring opening of the resulting dihydrofuran ring (11).