-
Something wrong with this record ?
Oxidative radical cyclizations of diketopiperazines bearing an amidomalonate unit. Heterointermediate reaction sequences toward the asperparalines and stephacidins
T. Amatov, M. Gebauer, R. Pohl, I. Cisařová, U. Jahn,
Language English Country England, Great Britain
Document type Journal Article
- MeSH
- Alkaloids chemistry MeSH
- Cyclization MeSH
- Diketopiperazines chemistry MeSH
- Molecular Structure MeSH
- Oxidation-Reduction MeSH
- Publication type
- Journal Article MeSH
A novel approach to the diazabicyclo[2.2.2]octane core of prenylated bridged diketopiperazine alkaloids is described by direct oxidative cyclizations of functionalized diketopiperazines mediated by ferrocenium hexafluorophosphate or the Mn(OAc)3•2H2O/Cu(OTf)2 system. Divergent reaction pathways take place depending on the substitution pattern of the substrates and the oxidation conditions such as temperature or the presence or absence of persistent radical TEMPO. For ester-substituted diketopiperazines, the ester group exerts a significant influence on the reaction outcome and stereochemistry of the radical cyclizations.
References provided by Crossref.org
- 000
- 00000naa a2200000 a 4500
- 001
- bmc17013427
- 003
- CZ-PrNML
- 005
- 20170428105627.0
- 007
- ta
- 008
- 170413s2016 enk f 000 0|eng||
- 009
- AR
- 024 7_
- $a 10.1080/10715762.2016.1223295 $2 doi
- 035 __
- $a (PubMed)27806645
- 040 __
- $a ABA008 $b cze $d ABA008 $e AACR2
- 041 0_
- $a eng
- 044 __
- $a enk
- 100 1_
- $a Amatov, Tynchtyk $u a Institute of Organic Chemistry and Biochemistry , Czech Academy of Sciences , Flemingovo namesti 2 , Prague 6, Czech Republic. $7 gn_A_00005309
- 245 10
- $a Oxidative radical cyclizations of diketopiperazines bearing an amidomalonate unit. Heterointermediate reaction sequences toward the asperparalines and stephacidins / $c T. Amatov, M. Gebauer, R. Pohl, I. Cisařová, U. Jahn,
- 520 9_
- $a A novel approach to the diazabicyclo[2.2.2]octane core of prenylated bridged diketopiperazine alkaloids is described by direct oxidative cyclizations of functionalized diketopiperazines mediated by ferrocenium hexafluorophosphate or the Mn(OAc)3•2H2O/Cu(OTf)2 system. Divergent reaction pathways take place depending on the substitution pattern of the substrates and the oxidation conditions such as temperature or the presence or absence of persistent radical TEMPO. For ester-substituted diketopiperazines, the ester group exerts a significant influence on the reaction outcome and stereochemistry of the radical cyclizations.
- 650 _2
- $a alkaloidy $x chemie $7 D000470
- 650 _2
- $a cyklizace $7 D003500
- 650 _2
- $a diketopiperaziny $x chemie $7 D054659
- 650 _2
- $a molekulární struktura $7 D015394
- 650 _2
- $a oxidace-redukce $7 D010084
- 655 _2
- $a časopisecké články $7 D016428
- 700 1_
- $a Gebauer, Martin $u a Institute of Organic Chemistry and Biochemistry , Czech Academy of Sciences , Flemingovo namesti 2 , Prague 6, Czech Republic.
- 700 1_
- $a Pohl, Radek $u a Institute of Organic Chemistry and Biochemistry , Czech Academy of Sciences , Flemingovo namesti 2 , Prague 6, Czech Republic.
- 700 1_
- $a Cisařová, Ivana $u b Department of Inorganic Chemistry, Faculty of Science , Charles University in Prague , Hlavova 2030/8 , Prague 2, Czech Republic.
- 700 1_
- $a Jahn, Ullrich $u a Institute of Organic Chemistry and Biochemistry , Czech Academy of Sciences , Flemingovo namesti 2 , Prague 6, Czech Republic.
- 773 0_
- $w MED00007947 $t Free radical research $x 1029-2470 $g Roč. 50, sup1 (2016), s. S6-S17
- 856 41
- $u https://pubmed.ncbi.nlm.nih.gov/27806645 $y Pubmed
- 910 __
- $a ABA008 $b sig $c sign $y a $z 0
- 990 __
- $a 20170413 $b ABA008
- 991 __
- $a 20170428105948 $b ABA008
- 999 __
- $a ok $b bmc $g 1199892 $s 974205
- BAS __
- $a 3
- BAS __
- $a PreBMC
- BMC __
- $a 2016 $b 50 $c sup1 $d S6-S17 $e 20161102 $i 1029-2470 $m Free radical research $n Free Radic Res $x MED00007947
- LZP __
- $a Pubmed-20170413
