Synthesis of the Tetracyclic Core of Berkelic Acid Using Gold(I)-Catalyzed Hydroarylation and Oxidative Radical Cyclizations

2012 ◽  
Vol 14 (23) ◽  
pp. 5820-5823 ◽  
Author(s):  
Margaret A. Brimble ◽  
Isabell Haym ◽  
Jonathan Sperry ◽  
Daniel P. Furkert
Keyword(s):  
Radical Cyclizations ◽  
Berkelic Acid ◽  
Tetracyclic Core

scholarly journals Biomimetic Synthesis of the Tetracyclic Core of Berkelic Acid

2007 ◽  
Vol 9 (11) ◽  
pp. 2071-2074 ◽  
Author(s):  
Jingye Zhou ◽  
Barry B. Snider
Keyword(s):  
Biomimetic Synthesis ◽  
Berkelic Acid ◽  
Tetracyclic Core

Synthesis of Spongidine A, D and Petrosaspongiolide L Methyl Ester Using Pyridine C-H Functionalization

2019 ◽  
Author(s):  
Florian Bartels ◽  
Manuela Weber ◽  
Mathias Christmann
Keyword(s):  
Natural Products ◽  
Methyl Ester ◽  
Hydrogen Atom ◽  
Phospholipase A2 ◽  
Late Stage ◽  
Hydrogen Atom Transfer ◽  
Ring System ◽  
Tetracyclic Core ◽  
Intramolecular Hydrogen ◽  
Phospholipase A2 Inhibitors

<div>An efficient strategy for the synthesis of the potent phospholipase A2 inhibitors spongidine A and D is presented. The tetracyclic core of the natural products was assembled via an intramolecular hydrogen atom transfer‐initiated Minisci reaction. A divergent late‐stage functionalization of the tetracyclic ring system was also used to achieve a concise synthesis of petrosaspongiolide L methyl ester.</div>

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.

The Study of Intramolecular Tandem Radical Cyclizations of Acylsilanes with Radicalphiles Attached on Silicon.

ChemInform ◽  
2005 ◽  
Vol 36 (26) ◽  
Author(s):  
Kuo-Hsiang Tang ◽  
Fang-Yu Liao ◽  
Yeun-Min Tsai
Keyword(s):  
Radical Cyclizations
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