2390-99-0

Usage

Uses

Used in Pharmaceutical Industry:
Chanoclavine is used as a pharmaceutical agent for its potential role in modulating dopamine receptors in the brain of rodents, which may have implications for the development of treatments for neurological disorders and conditions related to dopamine dysregulation.

InChI:InChI=1/C16H20N2O/c1-10(9-19)6-13-12-4-3-5-14-16(12)11(8-18-14)7-15(13)17-2/h3-6,8,13,15,17-19H,7,9H2,1-2H3/b10-6-/t13-,15-/m1/s1

Upstream product

• 158233-45-5 (4R,5R)-1-tert-butoxycarbonyl-4-(N-tert-butoxycarbonylamino)-5-vinyl-1,3,4,5-tetrahydrobenzindole 
• 158233-46-6 (4R,5R)-1-tert-butoxycarbonyl-4-(N-tert-butoxycarbonylamino)-5-formyl-1,3,4,5-tetrahydrobenzindole 
• 106507-95-3 (E)-4,5-cis-5-(2-hydroxymethyl-1-propen-1-yl)-4-methoxycarbonylamino-1,3,4,5-tetrahydrobenz[cd]indole 
• 106507-95-3 (E)-4,5-trans-5-(2-hydroxymethyl-1-propen-1-yl)-4-methoxycarbonylamino-1,3,4,5-tetrahydrobenz[cd]indole 
• 74447-21-5 1-(4-Methylamino-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl)-ethane-1,2-diol 
• 68156-97-8 (+/-)-6,7-seco-agroclavine 
• 106507-95-3 [(4S,5S)-5-((Z)-3-Hydroxy-2-methyl-propenyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid methyl ester 
• 107343-13-5 4,5-cis-5-(2-methyl-1-propen-1-yl)-4-amino-1,3,4,5-tetrahydrobenz[cd]indole 
• 51704-40-6 (+/-)-6-nor-chanoclavine-II 

Downstream Products

• 478-89-7 Pyroclavin 
• 569-26-6 festuclavine 
• 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 academic research and scientific papers

Catalase Involved in Oxidative Cyclization of the Tetracyclic Ergoline of Fungal Ergot Alkaloids

A dedicated enzyme for the formation of the central C ring in the tetracyclic ergoline of clinically important ergot alkaloids has never been found. Herein, we report a dual role catalase (EasC), unexpectedly using O2 as the oxidant, that catalyzes the oxidative cyclization of the central C ring from a 1,3-diene intermediate. Our study showcases how nature evolves the common catalase for enantioselective C-C bond construction of complex polycyclic scaffolds.

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.

Total Synthesis of (-)-Chanoclavine i and an Oxygen-Substituted Ergoline Derivative

An efficient and direct route to ergot alkaloid (-)-chanoclavine I (3) is described using the inexpensive compound (2R)-(+)-phenyloxirane (15) as a chiral pool in 13 steps with 17% overall yield. Key features of the synthesis include a palladium-catalyzed intramolecular aminoalkynylation of terminal olefin and a rhodium-catalyzed intramolecular [3 + 2] annulation. An oxygen-substituted ergoline derivative (-)-25 was also achieved by using the same strategy.

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.

Simple total syntheses of (-)-ergot alkaloids and their (+)-enantiomers by a common synthesis method utilizing optical resolution

The first and simple total syntheses of (-)-isochanoclavine-1 ((-)-1b), (-)-agroclavine ((-)-3), (-)-agroclavine-1 ((-)-4), and (-)-norchanoclavine-1 ((-)-5c) and their (+)-enantiomers are achieved from indole-3-carboxaldehyde (8) by a common synthesis method utilizing optical resolution. Absolute configuration of (-)-agroclavine-1 is determined to be 5R and 10S for the first time. Preparations of both enantiomers of chanoclavine-1 (1c) are also included.

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.

Syntheiss of (-)-chanoclavine I

The total enantioselective synthesis of (-)-chanoclavine I 2 in twelve steps from indole-4-carboxaldehyde 4 is described. The key-step 3 → 6 which involves the formation of the C ring by creation of the C5-C10 bond is catalyzed by a chiral palladium (0) complex. The chiral ergoline synthon 6 is produced with an excellent diastereo- and enantioselectivity (up to 95% ee).

Photocyclisation of Enamides. Part 35. New Total Syntheses of the Ergot Alkaloids (+/-)-Chanoclavine-I and (+/-)-isochanoclavine-I using a Fragmentation of 3-Amino Alcohols

A new synthetic route involving the fragmentation reaction of 3-amino alcohols for the total synthesis of 6,7-secoergoline alkaloids was developed and then successfully applied to the total syntheses of (+/-)-chanoclavine-I and (+/-)-isochanoclavine-I.

THE FIRST TOTAL SYNTHESIS OF (+/-)-CHANOCLAVINE-I ACID AND AN ALTERNATIVE TOTAL SYNTHESIS OF (+/-)-CHANOCLAVINE-I

The total synthesis of (+/-)-chanoclavine-I acid was achieved for the first time.An alternative total synthesis of (+/-)-chanoclavine-I was also reported.

A NOVEL SYNTHESIS OF (+/-)-ISOCHANOCLAVINE-I

Total synthesis of (+/-)-isochanoclavine-I (9) was achieved via the route involving fragmentation reaction of the 3-aminoalcohol 4.