Mechanism of Titanocene-Mediated Epoxide Opening through Homolytic Substitution

2007 ◽  
Vol 129 (5) ◽  
pp. 1359-1371 ◽  
Author(s):  
Andreas Gansäuer ◽  
Andriy Barchuk ◽  
Florian Keller ◽  
Martin Schmitt ◽  
Stefan Grimme ◽  
...  
Keyword(s):  
Epoxide Opening ◽  
Homolytic Substitution

An Endo ‐Selective Epoxide‐Opening Cascade for the Fast Assembly of the Polycyclic Core Structure of Marine Ladder Polyethers

2020 ◽  
Vol 59 (42) ◽  
pp. 18473-18478
Author(s):  
Feng‐Xing Li ◽  
Shu‐Jian Ren ◽  
Pei‐Fang Li ◽  
Peng Yang ◽  
Jin Qu
Keyword(s):  
Core Structure ◽  
Epoxide Opening

Synthesis of perfluoroalkylpyrroles by homolytic substitution with perfluoroalkyl radicals

1993 ◽  
Vol 34 (23) ◽  
pp. 3799-3800 ◽  
Author(s):  
Enrico Baciocchi ◽  
Ester Muraglia
Keyword(s):  
Homolytic Substitution

Synthesis of azaanthraquinones: homolytic substitution of pyridines

1982 ◽  
Vol 35 (7) ◽  
pp. 1451 ◽  
Author(s):  
DW Cameron ◽  
KR Deutscher ◽  
GI Feutrill ◽  
DE Hunt
Keyword(s):  
Ring Closure ◽  
Pyridine Derivatives ◽  
Derivatives Of ◽  
Substituted 1 ◽  
Homolytic Substitution

Synthesis of specific di- and tri-hydroxyazaanthraquinones by Friedel-Crafts procedures is limited by orientational ambiguity and by the lack of reactivity of pyridine derivatives in electrophilic acylation processes; however, suitable pyridines have been made to undergo radical benzoylation and benzylation at unsubstituted positions 2, 4 and 6. In particular, derivatives of pyridine-3-carbo-nitrile have been benzoylated at positions 2 and 4. Ring closure by intramolecular Houben-Hoesch reaction has then led to specifically substituted 1-and 2-azaanthraquinones and thence to the antibiotic bostrycoidin (1).

Chemical Diversity of Volatile Macrocylic Lactones from Frogs

Synlett ◽  
2021 ◽  
Author(s):  
Stefan Schulz ◽  
Dennis Poth ◽  
Pardha Saradhi Peram ◽  
Susann Hötling ◽  
Markus Menke ◽  
...  
Keyword(s):  
Biosynthetic Pathway ◽  
Chemical Diversity ◽  
Synthetic Methods ◽  
Epoxide Opening ◽  
Scientific Approach ◽  
Long Time ◽  
Fatty Acid Biosynthetic Pathway ◽  
Unsaturated Lactones ◽  
Male Specific ◽  
Synthetic Approaches

AbstractFor a long time, frogs were believed to communicate primarily via the acoustic channel, but during the last decades it became obvious that various lineages also use chemical communication. In this Account we present our research on the identification of volatile lactones from Madagascan Mantellidae and African Hyperoliidae frogs. Both possess male specific glands that can disseminate a range of volatile compounds. Key constituents are macrocyclic lactones. They show high variability in structure and occurrence. We focus here on the synthetic approaches we have used to clarify constitution and configuration of the glandular compounds. Key synthetic methods are ring-closing metathesis and nucleophilic epoxide opening. Often, but not always, the natural compounds occurs in amounts that excludes their investigation by NMR spectroscopy. Instead, we use GC/MS analysis, GC/IR, microreactions, and synthesis to identify such components. Several aspects of our work will be described giving some insight in our scientific approach.1 Introduction2 Macrocylic Lactones from the Fatty Acid Biosynthetic Pathway3 Unsaturated Lactones4 Terpenoid Lactones5 Macrolide Occurrence6 Conclusions

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