12626-18-5

Basic information

• Product Name: Fumitremorgin A
• Synonyms: Fumitremorgin A;FUMITREMORGENA
• CAS NO: 12626-18-5
• Molecular Formula: C32H41N3O7
• Molecular Weight: 579.69
• Mol File: 12626-18-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 762.1°Cat760mmHg
• Flash Point: 414.7°C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 2.03E-24mmHg at 25°C
• Refractive Index: 1.636
• CAS DataBase Reference: Fumitremorgin A(CAS DataBase Reference)
• NIST Chemistry Reference: Fumitremorgin A(12626-18-5)
• EPA Substance Registry System: Fumitremorgin A(12626-18-5)

Safety Data

• Hazardous Substances Data: 12626-18-5(Hazardous Substances Data)

Usage

Occurrence

A tremorgenic toxin isolated as a metabolite of AspergillusJurnigatus. It is highly toxic.

Definition

ChEBI: An organic heterohexacyclic compound that is a mycotoxic indole alkaloid obtained by prenylation of the 10-hydroxy group of verruculogen.

InChI:InChI=1/C32H41N3O7/c1-18(2)12-14-40-28-26-21-11-10-20(39-7)16-23(21)34-25(15-19(3)4)41-42-31(5,6)17-24(27(26)34)35-29(36)22-9-8-13-33(22)30(37)32(28,35)38/h10-12,15-16,22,24-25,28,38H,8-9,13-14,17H2,1-7H3/t22-,24-,25+,28-,32+/m0/s1

Upstream product

• 103321-52-4 (S)-N-(fluoren-9-ylmethoxycarbonyl)prolyl chloride 
• 71989-31-6 Fmoc-Pro-OH 
• 12771-72-1 verruculogen 
• 870-63-3 prenyl bromide 
• 107447-04-1 (S)-methyl 2-amino-3-(6-methoxy-1H-indol-3-yl)propanoate 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 141215-69-2 methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate 

Downstream Products

• 12771-72-1 verruculogen 
• 73395-18-3 C₂₇H₃₃N₃O₇ 
• 73367-07-4 C₃₂H₄₁N₃O₇ 

Relevant articles and documents

Total synthesis of verruculogen and fumitremorgin a enabled by ligand-controlled C-H borylation

Verruculogen and fumitremorgin A are bioactive alkaloids that contain a unique eight-membered endoperoxide. Although related natural products such as fumitremorgins B and C have been previously synthesized, we report the first synthesis of the more complex, endoperoxide-containing members of this family. A concise route to verruculogen and fumitremorgin A relied not only on a hydroperoxide/indole hemiaminal cyclization, but also on the ability to access the seemingly simple starting material, 6-methoxytryptophan. An iridium-catalyzed C-H borylation/Chan-Lam procedure guided by an N-TIPS group enabled the conversion of a tryptophan derivative into a 6-methoxytryptophan derivative, proving to be a general way to functionalize the C6 position of an N,C3-disubstituted indole for the synthesis of indole-containing natural products and pharmaceuticals.