862297-61-8

Basic information

• Product Name: 4-[(tert-butyldiphenylsilyloxy)methyl]indole-3-carboxaldehyde
• Synonyms: 4-[(tert-butyldiphenylsilyloxy)methyl]indole-3-carboxaldehyde
• CAS NO: 862297-61-8
• Molecular Weight: 413.591
• Mol File: 862297-61-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-[(tert-butyldiphenylsilyloxy)methyl]indole-3-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(tert-butyldiphenylsilyloxy)methyl]indole-3-carboxaldehyde(862297-61-8)
• EPA Substance Registry System: 4-[(tert-butyldiphenylsilyloxy)methyl]indole-3-carboxaldehyde(862297-61-8)

Safety Data

• Hazardous Substances Data: 862297-61-8(Hazardous Substances Data)

Upstream product

• 71516-34-2 2-((E)-2-Dimethylamino-vinyl)-3-nitro-benzoic acid ethyl ester 
• 59382-60-4 ethyl 2-methyl-3-nitrobenzoate 
• 50614-84-1 ethyl indole-4-carboxylate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 862297-60-7 4-[(tert-butyldiphenylsilyloxy)methyl]indole 
• 68-12-2 N,N-dimethyl-formamide 
• 1074-85-7 (1H-indol-4-yl)methanol 

Downstream Products

• 862297-56-1 4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indole-3-carboxaldehyde 
• 98664-90-5 ethyl (6aRS,9SR,9aSR)-hexahydro-7,7-dimethylisoindolo[4,5,6-cd]indole-9-carboxylate 
• 862297-58-3 ethyl 2-(4-nitrobenzenesulfonylamino)-5-methyl-3-[4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)-indole-3-yl]-4-hexenoate 
• 862297-63-0 ethyl 2-azido-5-methyl-3-{4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)-indol-3-yl}-hex-4-enoate 
• 862297-62-9 ethyl 5-methyl-3-{[4-(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indol-3-yl}hex-4-enoate 

Relevant articles and documents

A total synthesis of (±)-α-cyclopiazonic acid using a cationic cascade

The indolic terpene alkaloid α-cyclopiazonic acid 1 has been prepared in 11 steps from indole-4-methanol 6; the key step is a carbocationic cascade, terminated by a 4-nitrosulfonamide group and initiated by benzylic carbocation formation directly from the

The Knight route to cyclopiazonic acid: Enantioselective synthesis of a key intermediate

The indole alkaloid α-cyclopiazonic acid (CPA) is one of the few known inhibitors of sarco(endo)plasmic reticulum Ca2+-ATPase (SERCA) besides thapsigargin and artemisinin. Inhibitors of SERCA hold promise as novel anticancer and antimalarial drugs. Since its structure elucidation three racemic syntheses of α-cyclopiazonic acid have been published. We report now the first enantioselective and high yielding synthesis of a key-intermediate of the Knight synthesis, currently the most efficient route to CPA. Our synthesis is based on a diastereoselective 1,4-cuprate addition followed by an enolate azidation of an indolylacrylic acid modified with the Evans auxiliary.