1150-43-2

Basic information

• Product Name: (+/-)-isochanoclavine-II
• CAS NO: 1150-43-2
• Molecular Weight: 256.348
• Mol File: 1150-43-2.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: (+/-)-isochanoclavine-II(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-isochanoclavine-II(1150-43-2)
• EPA Substance Registry System: (+/-)-isochanoclavine-II(1150-43-2)

Safety Data

• Hazardous Substances Data: 1150-43-2(Hazardous Substances Data)

Upstream product

• 79133-62-3 4,5-trans-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenz-indole 
• 106488-71-5 E-4,5-cis-5-(2-hydroxymethyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole 
• 65846-99-3 methyl(E)-(4R^*,5R^*)-3-(4-methylamino-1,3,4,5-tetrahydrobenzindolyl-5-yl)-2-methylpropenoate 
• 106488-71-5 (E)-4,5-trans-5-(2-hydroxymethyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole 
• 51704-40-6 (+/-)-norchanoclavine-I 
• 51704-40-6 (+/-)-norisochanoclavine-I 
• 106488-71-5 (Z)-2-Methyl-3-((4S,5S)-4-nitro-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl)-prop-2-en-1-ol 

Downstream Products

• 548-42-5 (+/-)-Agroclavine 
• 95586-10-0 (+/-)-Agroclavine I 
• 77784-57-7 Acetic acid (E)-3-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-methyl-allyl ester 
• 77784-56-6 Acetic acid 2-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-ylmethyl]-allyl ester 

Relevant articles and documents

Biomimetic Total Syntheses of Clavine Alkaloids

Biomimetic total syntheses of either enantiomers of a number of ergot alkaloids, chanoclavine I (1b), chanoclavine I aldehyde (1c), pyroclavine (1e), festuclavine (1f), pibocin A (1g), 9-deacetoxyfumigaclavine C (1h), and fumigaclavine G (1i), have been achieved from seco-agroclavine (1a). The advanced intermediate for seco-agroclavine (1a) was synthesized via a key thiourea-catalyzed intramolecular nitronate addition onto α,β-unsaturated ester.

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 synthesis of optically active chanoclavine-I

The total synthesis of optically active chanoclavine-I, an ergot alkaloid, was accomplished using palladium-catalyzed intramolecular cyclization (Heck-reaction) as a key step. The conjugate ester (6) was obtained in 2 steps from optically active 4-bromotryptophan (10), and the cyclization of 6 proceeded smoothly without racemization to give the key intermediate, tricyclic tetrahydrobenz[c,d]indole derivative (7), in high yield.