951327-88-1

Basic information

• Product Name: 4-methoxy-D-tryptophan ethyl ester
• Synonyms: 4-methoxy-D-tryptophan ethyl ester
• CAS NO: 951327-88-1
• Molecular Weight: 262.309
• Mol File: 951327-88-1.mol

Chemical Properties

• CAS DataBase Reference: 4-methoxy-D-tryptophan ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methoxy-D-tryptophan ethyl ester(951327-88-1)
• EPA Substance Registry System: 4-methoxy-D-tryptophan ethyl ester(951327-88-1)

Safety Data

• Hazardous Substances Data: 951327-88-1(Hazardous Substances Data)

Upstream product

• 951327-81-4 3-(((2R,5S)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazin-2-yl)methyl)-4-methoxy-2-(trimethylsilyl)-1H-indole 

Downstream Products

• 951327-89-2 4-methoxy-D-tryptophan benzyl ester 
• 1094396-87-8 4-methoxy-D-tryptophan 
• 4098-40-2 mitragynine 
• 951327-91-6 (2R,6R,12bS,E)-benzyl 3-ethylidene-8-methoxy-2-(2-methoxy-2-oxoethyl)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-6-carboxylate 
• 951327-86-9 (1S,3R)-benzyl 2-((Z)-2-iodobut-2-enyl)-5-methoxy-1-((E)-4-methoxy-4-oxobut-2-enyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 
• 951327-90-5 (1S,3R,Z)-benzyl 2-(2-iodobut-2-enyl)-5-methoxy-1-(4-methoxy-4-oxo-3,3-bis(phenylthio)butyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 
• 951327-85-8 (R,Z)-benzyl 2-(2-iodobut-2-enylamino)-3-(4-methoxy-1H-indol-3-yl)propanoate 

Relevant articles and documents

Total synthesis of the opioid agonistic indole alkaloid mitragynine and the first total syntheses of 9-methoxygeissoschizol and 9-methoxy-N b-methylgeissoschizol

An enantiospecific method for the synthesis of 4-methoxytryptophan has been developed via a regiospecific Larock heteroannulation and employed for the first total syntheses of 9-methoxygeissoschizol and 9-methoxy-N b-methylgeissoschizol, as well as the total synthesis of the opioid agonistic alkaloid mitragynine. The asymmetric Pictet-Spengler reaction and a Ni(COD)2-mediated cyclization served as key steps.

General approach to the total synthesis of 9-methoxy-substituted indole alkaloids: Synthesis of mitragynine, as well as 9-methoxygeissoschizol and 9-methoxy-Nb-methylgeissoschizol

(Chemical Equation Presented) Herein, the full details of the synthesis of the 9-methoxy-substituted Corynanthe indole alkaloids mitragynine (1), 9-methoxygeissoschizol (3), and 9-methoxy-Nb-methylgeissoschizol (4) are described. Initially, an efficient synthetic route to the optically active 4-methoxytryptophan ethyl ester 20 on a multigram scale was developed via a Mori-Ban-Hegedus indole synthesis. The ethyl ester of D-4-methoxytryptophan 20 was obtained with a radical-mediated regioselective bromination of indoline 12 serving as a key step. Alternatively, the key 4-methoxytryptophan intermediate 22 could be synthesized by the Larock heteroannulation of aryl iodide 10b with the internal alkyne 21a. The use of the Boc-protected aniline 10b was crucial to the success of this heteroannulation. The α,β-unsaturated ester 6 was synthesized via the Pictet-Spengler reaction as the pivotal step. This was followed by a Ni(COD)2-mediated cyclization to set up the stereocenter at C-15. The benzyloxy group in 31 was removed to provide the intermediate ester 5. This chiral tetracyclic ester 5 was employed to accomplish the first total synthesis of 9-methoxygeissoschizol (3) and 9-methoxy-N b-methylgeissoschizol (4) as well as the opioid agonistic indole alkaloid mitragynine (1).