Concise asymmetric total synthesis of bruceolline J
Literature Information
Publication Date
2015-03-03
DOI
10.1039/C5QO00030K
Impact Factor
5.281
Authors
Dattatraya H. Dethe, Vijay Kumar B
View Original
Abstract
We have developed a concise biomimetic and asymmetric approach involving Sharpless asymmetric dihydroxylation and Lewis acid catalysed cyclopenta[b]annulation as key steps to synthesize (+)-bruceolline J, and a racemic approach employing an intramolecular rhodium carbenoid C–H insertion and highly regioselective gem-dimethylation reactions as key steps to synthesize bruceolline D, E along with (±)-bruceolline J.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![3,7-Di(1,1':3',1''-terphenyl-5'-yl)-10,11,12,13-tetrahydrodiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-ol 5-oxide structure](https://static.chemtradehub.com/structs/135/1352810-38-8-3f10.webp "3,7-Di(1,1':3',1''-terphenyl-5'-yl)-10,11,12,13-tetrahydrodiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-ol 5-oxide structure")
3,7-Di(1,1':3',1''-terphenyl-5'-yl)-10,11,12,13-tetrahydrodiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-ol 5-oxide
CAS Number:
1352810-38-8
Molecular Formula:
C53H39O4P
(1-(2-(Dimethylamino)ethyl)-1H-pyrazol-4-yl)boronic acid
CAS Number:
1086063-73-1
Molecular Formula:
C7H14BN3O2
![{3-[Bis(4-hydroxyphenyl)methyl]-1-[2-(dimethylamino)ethyl]-1H-indol-2-yl}[4-(2-chlorophenyl)-1-piperazinyl]methanone structure](https://static.chemtradehub.com/structs/170/170365-25-0-e4d7.webp "{3-[Bis(4-hydroxyphenyl)methyl]-1-[2-(dimethylamino)ethyl]-1H-indol-2-yl}[4-(2-chlorophenyl)-1-piperazinyl]methanone structure")
{3-[Bis(4-hydroxyphenyl)methyl]-1-[2-(dimethylamino)ethyl]-1H-indol-2-yl}[4-(2-chlorophenyl)-1-piperazinyl]methanone
CAS Number:
170365-25-0
Molecular Formula:
C36H37ClN4O3
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