67215-36-5

Basic information

• Product Name: iso-lysergic acid methyl ester
• Synonyms: iso-lysergic acid methyl ester
• CAS NO: 67215-36-5
• Molecular Weight: 282.342
• Mol File: 67215-36-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: iso-lysergic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: iso-lysergic acid methyl ester(67215-36-5)
• EPA Substance Registry System: iso-lysergic acid methyl ester(67215-36-5)

Safety Data

• Hazardous Substances Data: 67215-36-5(Hazardous Substances Data)

Upstream product

• 1449118-00-6 (S,E)-5-(4-bromo-1-tosyl-1H-indol-3-yl)pent-3-en-2-ol 
• 1449117-86-5 (S,E)-4-bromo-3-(4-((tert-butyldimethylsilyl)oxy)pent-2-en-1-yl)-1H-indole 
• 52488-36-5 4-bromo-1H-indole 
• 181271-32-9 4-bromo-1-(4-toluenesulfonyl)indole-3-carboxaldehyde 
• 50-00-0 formaldehyd 
• 87332-72-7 C₁₆H₁₆N₂O₂ 
• 1159774-78-3 (6aR)-4,7-di-tert-butyl 9-methyl 6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-4,7,9-tricarboxylate 
• 1159774-77-2 (6aR,10aS)-4,7-di-tert-butyl 9-methyl 6,6a-dihydroindolo[4,3-fg]quinoline-4,7,9(8H,10aH)-tricarboxylate 
• 1449118-02-8 (6aR,10aS)-di-tert-butyl 9-formyl-6,6a-dihydroindolo[4,3-fg]quinoline-4,7(8H,10aH)-dicarboxylate 
• 1449117-98-9 (6aR,10aS)-di-tert-butyl 9-((S)-1,2-dihydroxyethyl)-6,6a-dihydroindolo[4,3-fg]quinoline-4,7(8H,10aH)-dicarboxylate 
• 1449118-01-7 (6aR,10aS)-di-tert-butyl 9-((S)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecan-5-yl)-6,6a-dihydroindolo[4,3-fg]quinoline-4,7(8H,10aH)-dicarboxylate 
• 1449117-97-8 (6aR,10aS)-di-tert-butyl 9-((S)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecan-5-yl)-6,6a-dihydroindolo[4,3-fg]quinoline-4,7(8H,10aH)-dicarboxylate 
• 1449117-90-1 (2R,5R)-tert-butyl 2-((4-bromo-1-tosyl-1H-indol-3-yl)methyl)-5-((S)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecan-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate 
• 1449117-96-7 tert-butyl ((R)-1-(4-bromo-1-tosyl-1H-indol-3-yl)but-3-en-2-yl)((R)-2-((S)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecan-5-yl)but-3-en-1-yl)carbamate 

Relevant articles and documents

Erratum: Total synthesis of lysergic acid (Org. Lett. (2013) 15: 16 (4230-4233) DOI: 10.1021/ol4019562)

-

Total synthesis of lysergic acid

A total synthesis of lysergic acid was accomplished. Key features of our synthesis include stereoselective construction of the stereogenic centers at the allylic positions by using the Evans aldol reaction, and a sequential process with a ring-closing metathesis and an intramolecular Heck reaction to construct the C and D rings.

Enantioefficient synthesis of α-ergocryptine: First direct synthesis of (+)-lysergic acid

The first direct synthesis of (+)-lysergic acid (2a) suitable for scale-up has been achieved by the following reaction sequence. Bromoketones 4d or 4g were allowed to react with amine 5 followed by deprotection, and the resulting diketone 6c was transformed into the unsaturated ketone (±)-7 by the LiBr/Et3N system. Resolution afforded (+)-7, which was further transformed by Schoellkopfs method into the mixture of esters 2e and 2f. Upon hydrolysis the latter mixture afforded (+)-2a. The peptide part of α-ergocryptine (1) was prepared according to the Sandoz method; the stereoefficiency, however, has been significantly improved by applying a new resolution method and recycling the undesired enantiomer. Coupling the peptide part with lysergic acid afforded 1. Having synthetic (+)-7 in hand, we can claim the total synthesis of all the alkaloids which were prepared earlier from (+)-7 that had been obtained through degradation of natural lysergic acid.