1369969-31-2

Basic information

• Product Name: 1,8-di-tert-butyl 2-methyl (2S,3aR,8aR)-3a-(4-methoxyphenyl)-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate
• Synonyms: 1,8-di-tert-butyl 2-methyl (2S,3aR,8aR)-3a-(4-methoxyphenyl)-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate
• CAS NO: 1369969-31-2
• Molecular Weight: 524.614
• Mol File: 1369969-31-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,8-di-tert-butyl 2-methyl (2S,3aR,8aR)-3a-(4-methoxyphenyl)-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-di-tert-butyl 2-methyl (2S,3aR,8aR)-3a-(4-methoxyphenyl)-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate(1369969-31-2)
• EPA Substance Registry System: 1,8-di-tert-butyl 2-methyl (2S,3aR,8aR)-3a-(4-methoxyphenyl)-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate(1369969-31-2)

Safety Data

• Hazardous Substances Data: 1369969-31-2(Hazardous Substances Data)

Upstream product

• 696-62-8 para-iodoanisole 
• 1064604-21-2 methyl (2S,3aR,8aR)-[3a-bromo-(1,2,3,3a,8,8a)-hexahydropyrrolo[2,3-b]indole-1,8-di-tertbutoxycarbonyl]-2-carboxylate 
• 100-66-3 methoxybenzene 
• 96238-68-5 tert-butyl (+)-(S)-3-[2-(tert-butoxycarbonylamino)-3-methoxy-3-oxopropyl]-1H-indole-1-carboxylate 

Relevant articles and documents

Ni-Catalyzed Reductive Coupling of Electron-Rich Aryl Iodides with Tertiary Alkyl Halides

This work illustrates the reductive coupling of electron-rich aryl halides with tertiary alkyl halides under Ni-catalyzed cross-electrophile coupling conditions, which offers an efficient protocol for the construction of all carbon quaternary stereogenic centers. The mild and easy-to-operate reaction tolerates a wide range of functional groups. The utility of this method is manifested by the preparation of cyclotryptamine derivatives, wherein successful incorporation of 7-indolyl moieties is of particular interest as numerous naturally occurring products are composed of these key scaffolds. DFT calculations have been carried out to investigate the proposed radical chain and double oxidative addition pathways, which provide useful mechanistic insights into the part of the reaction that takes place in solution.

Silver-promoted Friedel-Crafts reaction: Concise total synthesis of (-)-ardeemin, (-)-acetylardeemin and (-)-formylardeemin

Total syntheses of multidrug resistant inhibitors (-)-acetylardeemin 2a, (-)-ardeemin 2b, and (-)-formylardeemin 3 have been achieved within 10 steps starting from bromopyrroloinoline 13. The key step involves direct alkylation of 13 with prenyl tributylstannane 11 to yield 12via a silver-promoted asymmetric Friedel-Crafts reaction. Highly efficient installation of the isoprenyl group allowed excellent overall yield. Moreover, the substrate scope of the asymmetric Friedel-Crafts reaction of 13 was expanded to include a variety of arenes 14 to afford natural product-like library analogues 15. The Royal Society of Chemistry 2012.