Intramolecular Vinyl Radical Cyclization Reactions of cyclohexadienes derived from sequential additions to (arene)(tricarbonyl)chromium complexes. Preliminary communication

1996 ◽  
Vol 79 (6) ◽  
pp. 1533-1536 ◽  
Author(s):  
Dov Beruben ◽  
E. Peter Kündig
Keyword(s):  
Radical Cyclization ◽  
Chromium Complexes ◽  
Cyclization Reactions ◽  
Vinyl Radical ◽  
Preliminary Communication

scholarly journals Activation modes in biocatalytic radical cyclization reactions

2021 ◽  
Author(s):  
Yuxuan Ye ◽  
Haigen Fu ◽  
Todd K Hyster
Keyword(s):  
Heme Iron ◽  
Radical Cyclization ◽  
Cytochrome P450 Monooxygenases ◽  
Radical Cyclizations ◽  
Cyclization Reactions ◽  
Complex Molecules ◽  
P450 Monooxygenases ◽  
Non Heme Iron ◽  
Essential Reactions ◽  
Isopenicillin N

Abstract Radical cyclizations are essential reactions in the biosynthesis of secondary metabolites and the chemical synthesis of societally valuable molecules. In this review, we highlight the general mechanisms utilized in biocatalytic radical cyclizations. We specifically highlight cytochrome P450 monooxygenases (P450s) involved in the biosynthesis of mycocyclosin and vancomycin, non-heme iron- and α-ketoglutarate-dependent dioxygenases (Fe/αKGDs) used in the biosynthesis of kainic acid, scopolamine, and isopenicillin N, and radical S-adenosylmethionine (SAM) enzymes that facilitate the biosynthesis of oxetanocin A, menaquinone, and F420. Beyond natural mechanisms, we also examine repurposed flavin-dependent ‘ene’-reductases (ERED) for non-natural radical cyclization. Overall, these general mechanisms underscore the opportunity for enzymes to augment and enhance the synthesis of complex molecules using radical mechanisms.

Radical cyclization reactions of 4-bromo vinylogous-esters, vinylogous-amides and enones

1997 ◽  
pp. 239-240 ◽  
Author(s):  
Chin-Kang Sha ◽  
Wei-Hong Tseng ◽  
Kuan-Tsau Huang ◽  
Kuan-Miao Liu ◽  
Herng-Yih Lin ◽  
...  
Keyword(s):  
Radical Cyclization ◽  
Cyclization Reactions ◽  
Vinylogous Esters ◽  
Vinylogous Amides

scholarly journals A Vinyl Radical Cyclization Route to Hydroxycyclohexene Fused Carbocycles

2016 ◽  
Vol 28 (1) ◽  
pp. 233-234 ◽  
Author(s):  
Shiladitya Chaudhuri ◽  
Susama Maity ◽  
Mahua Roy ◽  
Paramita Ray ◽  
Jayanta K. Ray
Keyword(s):  
Radical Cyclization ◽  
Vinyl Radical

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.

Copper(I)-Catalyzed Chlorine Atom Transfer Radical Cyclization Reactions of Unsaturated α-Chloro β-Keto Esters

2006 ◽  
Vol 8 (25) ◽  
pp. 5757-5760 ◽  
Author(s):  
Dan Yang ◽  
Yi-Long Yan ◽  
Bao-Fu Zheng ◽  
Qiang Gao ◽  
Nian-Yong Zhu
Keyword(s):  
Chlorine Atom ◽  
Radical Cyclization ◽  
Atom Transfer ◽  
Cyclization Reactions ◽  
Keto Esters ◽  
Atom Transfer Radical Cyclization

Intramolecular Radical Cyclization of Vinyl, Aryl and Alkyl Halides Using Catalytic Amount of Bis-tri-n-butyltin Oxide/Sodium Borohydride: A Novel Entry to Functionalized Carbocycles

Synlett ◽  
2015 ◽  
Vol 26 (08) ◽  
pp. 1055-1058 ◽  
Author(s):  
Namasivayam Palani ◽  
Sengottuvelan Balasubramanian ◽  
Tarur Dinesh
Keyword(s):  
Sodium Borohydride ◽  
Catalytic Amount ◽  
Radical Cyclization ◽  
Alkyl Halides ◽  
Cyclization Reactions

We wish to report a facile method in which a catalytic amount of bis-tri-n-butyltinoxide (TBTO) in the presence of sodium borohydride efficiently brings about the intramolecular radical cyclization of a variety of vinyl, aryl and alkyl halides to their corresponding functionalized bicyclic and tricyclic carbocycle frameworks. The methodology obviates the need for stoichiometric amounts of tin reagent normally required for radical cyclization reactions.

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