Stereochemical control in hex-5-enyl radical cyclizations: axial vs equatorial 2-(1-but-3-enyl)cyclohexyl radicals

1989 ◽  
Vol 111 (1) ◽  
pp. 296-300 ◽  
Author(s):  
T. V. RajanBabu ◽  
Tadamichi Fukunaga
Keyword(s):  
Radical Cyclizations ◽  
Stereochemical Control

Stereochemical control in hex-5-enyl radical cyclizations: from carbohydrates to carbocycles. 3

1989 ◽  
Vol 111 (5) ◽  
pp. 1759-1769 ◽  
Author(s):  
T. V. RajanBabu ◽  
Tadamichi Fukunaga ◽  
G. S. Reddy
Keyword(s):  
Radical Cyclizations ◽  
Stereochemical Control

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.

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