A convergent approach to the tetracyclic core of atisane diterpenes

2016 ◽  
Vol 27 (1) ◽  
pp. 59-62 ◽  
Author(s):  
De-Lin Chen ◽  
Feng-Peng Wang ◽  
Xiao-Yu Liu
Keyword(s):  
Tetracyclic Core ◽  
Convergent Approach

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>

Probing the Versatility of Shape-Persistent Tetraphenylmethane Dendrimers by Modification of the Skeleton

2019 ◽  
Author(s):  
Julio Ignacio Urzúa ◽  
Sandra Campana ◽  
Massimo Lazzari ◽  
Mercedes Torneiro
Keyword(s):  
Design Principle ◽  
Focal Point ◽  
Sonogashira Coupling ◽  
Terminal Alkyne ◽  
Double Phase ◽  
Rigid Rod ◽  
Convergent Approach ◽  
First And Second Generation ◽  
Oxidative Homocoupling ◽  
Hypercrosslinked Polymers

Tetraphenylmethane has emerged as a recurrent building block for advanced porous materials such as COFs, PAFs and hypercrosslinked polymers. Guided by a similar design principle, we have previously synthesized shape-persistent dendrimers with tetraphenylmethane nodes and ethynylene linkers. Here we report the generality of our approach by describing new dendritic architectures built from tetraphenylmethane. First, we prepared expanded dendrimers where the tetrahedral units are bonded through larger rigid rod spacers. Among the different synthetic strategies tested, the convergent route, with alternating steps of Pd-catalyzed Sonogashira coupling and alkyne activation by removal of TMS masking groups, efficiently afforded the first- and second-generation dendrimers. A second type of compounds having a linear diyne at the core is also described. The dendrimers of generations 1-2 were also synthesized by a convergent approach, with the diyne being assembled in the last step of the synthesis by a Glaser oxidative homocoupling of the corresponding dendrons bearing a terminal alkyne at the focal point. A third-generation dendrimer was also successfully prepared by a double-phase strategy.<br>

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