116005-49-3

Basic information

• Product Name: tert-butyl 3-({(6′R,7′R,8a′R)-10-(4′′-methoxybenzyl)-5′,9′-dioxo-7′-(prop-1′′′-en-2′′′-yl)hexahydro-1H-6′,8a′-(epiminomethano)indolizin-6′-yl}methyl)-1H-indole-1-carboxylate
• Synonyms: tert-butyl 3-({(6′R,7′R,8a′R)-10-(4′′-methoxybenzyl)-5′,9′-dioxo-7′-(prop-1′′′-en-2′′′-yl)hexahydro-1H-6′,8a′-(epiminomethano)indolizin-6′-yl}methyl)-1H-indole-1-carboxylate
• CAS NO: 116005-49-3
• Molecular Weight: 569.701
• Mol File: 116005-49-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: tert-butyl 3-({(6′R,7′R,8a′R)-10-(4′′-methoxybenzyl)-5′,9′-dioxo-7′-(prop-1′′′-en-2′′′-yl)hexahydro-1H-6′,8a′-(epiminomethano)indolizin-6′-yl}methyl)-1H-indole-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 3-({(6′R,7′R,8a′R)-10-(4′′-methoxybenzyl)-5′,9′-dioxo-7′-(prop-1′′′-en-2′′′-yl)hexahydro-1H-6′,8a′-(epiminomethano)indolizin-6′-yl}methyl)-1H-indole-1-carboxylate(116005-49-3)
• EPA Substance Registry System: tert-butyl 3-({(6′R,7′R,8a′R)-10-(4′′-methoxybenzyl)-5′,9′-dioxo-7′-(prop-1′′′-en-2′′′-yl)hexahydro-1H-6′,8a′-(epiminomethano)indolizin-6′-yl}methyl)-1H-indole-1-carboxylate(116005-49-3)

Safety Data

• Hazardous Substances Data: 116005-49-3(Hazardous Substances Data)

Upstream product

• 116005-51-7 (-)-2-(R)-allyl-2-<(4-methoxybenzyl)carboxamido>pyrrolidine 
• 116005-52-8 (-)-2,5-diketo-6-(R)-allyl-4-(methoxybenzyl)-1,4-diazabicyclo<4.3.0>nonane 
• 116051-29-7 (-)-2,5-diketo-6-(R)-(formylmethyl)-4-(4-methoxybenzyl)-1,4-diazabicyclo<4.3.0>nonane 
• 124339-51-1 6-<(2E)-4-keto-3-methylbut-2-enyl>-2,5-diketo-4-(4-methoxybenzyl)-1,4-diazabicyclo<4.3.0>nonane 
• 116051-30-0 6-<(2E)-4-hydroxy-3-methylbut-2-enyl>-2,5-diketo-4-(4-methoxybenzyl)-1,4-diazabicyclo<4.3.0>nonane 
• 124268-77-5 (-)-6-(R)-<(2E)-4-<(tert-butyldimethylsilyl)oxy>3-methylbut-2-enyl>-2,5-diketo-4-(4-methoxybenzyl)-1,4-diazabicyclo<4.3.0>nonane 
• 116005-50-6 6-<(2E)-4-<(tert-butyldimethylsilyl)oxy>but-2-enyl>-3-(carbomethoxy)-4-(4-methoxybenzyl)-1,4-diazabicyclo<4.3.0>nonane 
• 124268-82-2 (-)-6-(R)-<(2E)-4-<(tert-butyldimethylsilyl)oxy>3-methylbut-2-enyl>-2,5-diketo-3-(R)-<(3-indolyl)methyl>-4-(4-methoxybenzyl)-1,4-diazabicyclo<4.3.0>nonane 
• 1024013-31-7 C₃₄H₄₁N₃O₅ 
• 2393-23-9 4-methoxy-benzylamine 
• 116005-53-9 (+)-6-(R)-<(2E)-4-<(tert-butyldimethylsilyl)oxy>3-methylbut-2-enyl>-3-(R)(carbometoxy)-2,5-diketo-3-<(3-indolyl)methyl>-4-(4-methoxybenzyl)-1,4-diazabicyclo<4.3.0>nonane 
• 124268-83-3 3-[(R)-8a-((E)-4-Hydroxy-3-methyl-but-2-enyl)-2-(4-methoxy-benzyl)-1,4-dioxo-octahydro-pyrrolo[1,2-a]pyrazin-3-ylmethyl]-indole-1-carboxylic acid tert-butyl ester 
• 81286-83-1 (2R,5R)-5-allyl-2-tert-butyl-1-aza-3-oxabicyclo<3.3.0>octan-4-one 
• 87-52-5 3-(Dimethylaminomethyl)indole 

Relevant articles and documents

The cascade radical cyclisation approach to prenylated alkaloids: Synthesis of stephacidin A and notoamide B

A strategy for the synthesis of members of the prenylated indole alkaloid family is described, which involves a radical cascade process of an appropriately substituted diketopiperazine (DKP) core structure. Several approaches to the generation of the initial radical were explored, with the most successful involving treatment of a sulfenyl substituted DKP under classical reductive conditions by heating with Bu3SnH and a radical initiator. The required, fully substituted, radical precursor DKP structures were prepared using regio- and stereocontrolled enolate chemistry of simpler proline-tryptophan derived DKPs. The new approach allowed rapid access to a key polycyclic indoline structure, which was converted into either of the natural products stephacidin A or notoamide B.

Asymmetric, stereocontrolled total synthesis of (-)-brevianamide B

The asymmetric, stereocontrolled total synthesis of (-)-brevianamide B (2) is described. The synthesis features a stereocontrolled intramolecular SN2′ cyclization to construct the central bicyclo[2.2.2] nucleus. A synthetic route to C-10-epibre