scholarly journals Biomimetic Synthesis of Hitorins A and B via an Intermolecular Alkoxy Radical-Olefin Coupling Cascade

2019 ◽  
Author(s):  
Xiaohuan Li ◽  
Tianran Zhai ◽  
Ping He ◽  
Zheng Wei ◽  
Zhang Wang
Keyword(s):  
Cascade Reaction ◽  
Oxidative Cleavage ◽  
Experimental Results ◽  
Biomimetic Synthesis ◽  
Alkoxy Radical ◽  
Radical Oxidation ◽  
Olefin Coupling ◽  
Radical Cascade ◽  
Grob Fragmentation

A biomimetic synthesis of hitorins A and B was achieved based on our modified biosynthetic proposal. In our synthesis, a radical cascade reaction between an alkoxy radical, generated from a hydroperoxide, and a monoterpene (+)-sabinene renders the tetrahydrofuran ring of hitorins A and B. In addition, experimental results supported that the oxidative cleavage of the tetrasubstituted olefin in a key intermediate is via a radical oxidation cascade followed by a Grob fragmentation.<br>

scholarly journals Biomimetic Synthesis of Hitorins A and B via an Intermolecular Alkoxy Radical-Olefin Coupling Cascade

2019 ◽  
Author(s):  
Xiaohuan Li ◽  
Tianran Zhai ◽  
Ping He ◽  
Zheng Wei ◽  
Zhang Wang
Keyword(s):  
Cascade Reaction ◽  
Oxidative Cleavage ◽  
Experimental Results ◽  
Biomimetic Synthesis ◽  
Alkoxy Radical ◽  
Radical Oxidation ◽  
Olefin Coupling ◽  
Radical Cascade ◽  
Grob Fragmentation

A biomimetic synthesis of hitorins A and B was achieved based on our modified biosynthetic proposal. In our synthesis, a radical cascade reaction between an alkoxy radical, generated from a hydroperoxide, and a monoterpene (+)-sabinene renders the tetrahydrofuran ring of hitorins A and B. In addition, experimental results supported that the oxidative cleavage of the tetrasubstituted olefin in a key intermediate is via a radical oxidation cascade followed by a Grob fragmentation.<br>

A metal-free radical cascade reaction of phosphine oxides with 2-aryloxy phenylacetylenes to assemble diphosphonyl xanthene derivatives

2021 ◽  
Author(s):  
Tao Fan ◽  
Yan Liu ◽  
Caina Jiang ◽  
Yanli Xu ◽  
Yan-Yan Chen
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Cascade Reaction ◽  
Phosphine Oxides ◽  
Metal Free ◽  
Mild Conditions ◽  
Xanthene Derivatives ◽  
Reaction Proceeds ◽  
Radical Cascade

A radical cascade reaction of 2-aryloxy phenylacetylene with phosphine oxides promoted by K2S2O8 was developed, provided diphosphonyl xanthenes as products. This reaction proceeds under transition metal-free and mild conditions with...

Highly Cumulated Radical Cascade Reaction of aza-1,6-Enyenes: Stereoselective Synthesis of exo -Methylene Piperidines

2020 ◽  
Vol 2020 (11) ◽  
pp. 1700-1707
Author(s):  
Akio Kamimura ◽  
Tomoyuki Itaya ◽  
Tatsuro Yoshinaga ◽  
Ryo Nozawa ◽  
Takuji Kawamoto ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Cascade Reaction ◽  
Radical Cascade

scholarly journals Preparation of optically active bicyclodihydrosiloles by a radical cascade reaction

2013 ◽  
Vol 9 ◽  
pp. 1326-1332 ◽  
Author(s):  
Koichiro Miyazaki ◽  
Yu Yamane ◽  
Ryuichiro Yo ◽  
Hidemitsu Uno ◽  
Akio Kamimura
Keyword(s):  
Silicon Atom ◽  
Cascade Reaction ◽  
Radical Cyclization ◽  
Optically Active ◽  
Unsaturated Ester ◽  
Terminal Alkyne ◽  
Silyl Radical ◽  
Vinyl Radical ◽  
Radical Cascade ◽  
Carbonyl Radical

Bicyclodihydrosiloles were readily prepared from optically active enyne compounds by a radical cascade reaction triggered by tris(trimethylsilyl)silane ((Me3Si)3SiH). The reaction was initiated by the addition of a silyl radical to an α,β-unsaturated ester, forming an α-carbonyl radical that underwent radical cyclization to a terminal alkyne unit. The resulting vinyl radical attacked the silicon atom in an SHi manner to give dihydrosilole. The reaction preferentially formed trans isomers of bicyclosiloles with an approximately 7:3 to 9:1 selectivity.

scholarly journals Molecular orbital study of the oxidation of steroidal phenols into quinols and epoxyquinols

2000 ◽  
Vol 65 (7) ◽  
pp. 491-496 ◽  
Author(s):  
Zoran Markovic ◽  
Bogdan Solaja ◽  
Dragan Milic ◽  
Ivan Juranic ◽  
Miroslav Gasic
Keyword(s):  
Activation Energy ◽  
Molecular Orbital ◽  
Experimental Results ◽  
Full Agreement ◽  
Radical Oxidation ◽  
Molecular Orbital Study ◽  
Orbital Study ◽  
Oxidation Of Phenols

The MO study showed that the radical oxidation of phenols into quinols occurs readily. Further radical oxidation (in the m-CPBA/(BzO)2/hv system) of quinols occurs through appropriate biradical species with an activation energy of 79.5 kJ/mol yielding syn-epoxyquinols. The stereochemical outcome presented in this study is in full agreement with the experimental results.

Catalytic Radical Cascade Cyclization of Alkene-Tethered Enones to Fused Bicyclic Cyclopropanols

2021 ◽  
Author(s):  
Ying Xie ◽  
Wei Huang ◽  
Song Qin ◽  
Shaomin Fu ◽  
Bo Liu
Keyword(s):  
Hydrogen Atom ◽  
Cascade Reaction ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Trimethyl Borate ◽  
Cascade Cyclization ◽  
Radical Cascade ◽  
Privileged Scaffolds

An unprecedented hydrogen atom transfer-triggered intramolecular cascade reaction between alkene and enone is developed, using Fe(acac)3, PhSiH2(Oi-Pr) and trimethyl borate, to efficiently construct cis-fused bicyclic cyclopropanols, privileged scaffolds often found...

Recent applications of radical cascade reaction in the synthesis of functionalized 1-indenones

2019 ◽  
Vol 30 (7) ◽  
pp. 1361-1368 ◽  
Author(s):  
Yinli Zhang ◽  
Kai Sun ◽  
Qiyan Lv ◽  
Xiaolan Chen ◽  
Lingbo Qu ◽  
...  
Keyword(s):  
Cascade Reaction ◽  
Radical Cascade

Manganese(ii)-catalyzed modular synthesis of isoquinolines from vinyl isocyanides and hydrazines

2016 ◽  
Vol 3 (4) ◽  
pp. 516-521 ◽  
Author(s):  
Hong Mao ◽  
Mingchun Gao ◽  
Bingxin Liu ◽  
Bin Xu
Keyword(s):  
Cascade Reaction ◽  
Modular Synthesis ◽  
Radical Cascade

An efficient manganese(ii)-catalyzed oxidative radical cascade reaction was developed from vinyl isocyanides and hydrazines leading to the modular synthesis of multi-substituted isoquinolines, phenanthridines and pyrrolo[1,2-a]quinoxalines.

scholarly journals The Introduction of the Radical Cascade Reaction into Polymer Chemistry: A One-Step Strategy for Synchronized Polymerization and Modification

iScience ◽  
2020 ◽  
Vol 23 (3) ◽  
pp. 100902 ◽  
Author(s):  
Nengbo Zhu ◽  
Mong-Feng Chiou ◽  
Haigen Xiong ◽  
Min Su ◽  
Muqiao Su ◽  
...  
Keyword(s):  
Cascade Reaction ◽  
Polymer Chemistry ◽  
Radical Cascade ◽  
One Step

Visible-light-mediated radical cascade reaction: synthesis of 3-bromocoumarins from alkynoates

2017 ◽  
Vol 15 (41) ◽  
pp. 8820-8826 ◽  
Author(s):  
Shangbiao Feng ◽  
Jinlai Li ◽  
Zaimin Liu ◽  
Haiyu Sun ◽  
Hongliang Shi ◽  
...  
Keyword(s):  
Visible Light ◽  
Cascade Reaction ◽  
Radical Addition ◽  
Reaction Synthesis ◽  
Radical Cascade

The development of a visible-light mediated bromo radical addition/spirocyclization/ester migration cascade reaction to generate 3-bromocoumarins from alkynoates is reported.

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