Allylsilanes in organic synthesis; An approach to the stereoselective synthesis of units for natural product synthesis

1990 ◽  
Vol 31 (7) ◽  
pp. 1059-1062 ◽  
Author(s):  
Patrick J. Murphy ◽  
Garry Procter
Keyword(s):  
Natural Product ◽  
Organic Synthesis ◽  
Stereoselective Synthesis ◽  
Natural Product Synthesis

scholarly journals Synthesis of spirocyclic scaffolds using hypervalent iodine reagents

2018 ◽  
Vol 14 ◽  
pp. 1778-1805 ◽  
Author(s):  
Fateh V Singh ◽  
Priyanka B Kole ◽  
Saeesh R Mangaonkar ◽  
Samata E Shetgaonkar
Keyword(s):  
Organic Chemistry ◽  
Heavy Metals ◽  
Natural Product ◽  
Organic Synthesis ◽  
Stereoselective Synthesis ◽  
Natural Product Synthesis ◽  
Hypervalent Iodine ◽  
Toxic Heavy Metals ◽  
Synthetic Organic Chemistry ◽  
The Past

Hypervalent iodine reagents have been developed as highly valuable reagents in synthetic organic chemistry during the past few decades. These reagents have been identified as key replacements of various toxic heavy metals in organic synthesis. Various synthetically and biologically important scaffolds have been developed using hypervalent iodine reagents either in stoichiometric or catalytic amounts. In addition, hypervalent iodine reagents have been employed for the synthesis of spirocyclic scaffolds via dearomatization processes. In this review, various approaches for the synthesis of spirocyclic scaffolds using hypervalent iodine reagents are covered including their stereoselective synthesis. Additionally, the applications of these reagents in natural product synthesis are also covered.

scholarly journals A General Copper-based Photoredox Catalyst for Organic Synthesis: Scope, Application in Natural Product Synthesis and Mechanistic Insights

2018 ◽  
Vol 72 (9) ◽  
pp. 621-629 ◽  
Author(s):  
Christopher Deldaele ◽  
Bastien Michelet ◽  
Hajar Baguia ◽  
Sofia Kajouj ◽  
Eugenie Romero ◽  
...  
Keyword(s):  
Natural Product ◽  
Organic Synthesis ◽  
Natural Product Synthesis

Regioselective N-alkylation of (2-chloroquinolin-3-yl) methanol with N-heterocyclic compounds using the Mitsunobu reagent

2011 ◽  
Vol 65 (3) ◽  
Author(s):  
Selvaraj Roopan ◽  
Fazlur-Rahman Khan ◽  
Jong Jin
Keyword(s):  
Natural Product ◽  
Organic Synthesis ◽  
Heterocyclic Compounds ◽  
Building Blocks ◽  
Natural Product Synthesis ◽  
Mitsunobu Reaction ◽  
Reaction Conditions ◽  
Diethyl Azodicarboxylate ◽  
Nitrogen Heterocyclic

AbstractThe Mitsunobu reaction is a well-established fundamental reaction and has been widely applied in organic synthesis. In this paper, under Mitsunobu conditions dehydration proceeds between (2-chloroquinolin-3-yl)methanol and nitrogen heterocyclic compounds such as quinazolinone, pyrimidone, 2-oxoquinoline in dry THF in the presence of triethylamine, triphenylphosphane and diethyl azodicarboxylate to give the corresponding products. As part of our recent research, we attempted to couple two N-heterocyclic compounds under Mitsunobu reaction conditions to provide efficient building blocks for natural product synthesis.

Highly stereoselective synthesis of the indolo[2,3-a]quinolizine ring system and application to indole natural product synthesis

2004 ◽  
Vol 45 (38) ◽  
pp. 7103-7105 ◽  
Author(s):  
Steven M. Allin ◽  
Christopher I. Thomas ◽  
James E. Allard ◽  
Kevin Doyle ◽  
Mark R.J. Elsegood
Keyword(s):  
Natural Product ◽  
Stereoselective Synthesis ◽  
Ring System ◽  
Natural Product Synthesis

scholarly journals σ-Bond Hydroboration of Cyclopropanes

2020 ◽  
Author(s):  
Hiroki Kondo ◽  
Shin Miyamura ◽  
Chisa Kobayashi ◽  
Arifin ◽  
Stephan Irle ◽  
...  
Keyword(s):  
Double Bond ◽  
Natural Product ◽  
Organic Synthesis ◽  
Bond Cleavage ◽  
Cross Coupling ◽  
High Reactivity ◽  
Natural Product Synthesis ◽  
Theoretical Studies ◽  
Single Bond

Hydroboration of alkenes is a classical reaction in organic synthesis, in which alkenes react with boranes to give alkylboranes, with subsequent oxidation resulting in alcohols. The double bond (π-bond) of alkenes can be readily reacted with boranes owing to its high reactivity. However, the single bond (σ-bond) of alkanes has never been reacted. To pursue the development of σ-bond cleavage, we selected cyclopropanes as model substrates since they present a relatively weak σ-bond. Herein, we describe an iridium-catalyzed hydroboration of cyclopropanes, resulting in β-methyl alkylboronates. These unusually branched boronates can be derivatized by oxidation or cross-coupling chemistry, accessing “designer” products that are desired by practitioners of natural product synthesis and medicinal chemistry. Furthermore, mechanistic investigations and theoretical studies revealed the enabling role of the catalyst.

Alkyne-Forming Furan Fragmentation: A General Method to Convert Furans into Alkynoic Acids

Synlett ◽  
2019 ◽  
Vol 30 (06) ◽  
pp. 642-646
Author(s):  
Jinghan Gui ◽  
Jiachen Deng
Keyword(s):  
Reaction Mechanism ◽  
Double Bond ◽  
Singlet Oxygen ◽  
Natural Product ◽  
Organic Synthesis ◽  
Bond Cleavage ◽  
Historical Context ◽  
Natural Product Synthesis ◽  
Fragmentation Reaction ◽  
General Method

Furans are readily available and highly reactive heterocycles that serve as versatile four-carbon synthons in organic synthesis. Recently, we discovered that furans, upon oxidation with singlet oxygen, can be transformed into alkynes via dual C–C double-bond cleavage. This Synpacts article presents an overview of the historical context and the development of this furan fragmentation reaction. We also discuss its application in natural product synthesis and a plausible reaction mechanism.1 Introduction2 Background of Alkyne-Forming Furan Fragmentation3 Reaction Development4 Conclusion

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