Transition-Metal-Catalyzed Reactions Involving Arynes

Synthesis ◽  
2017 ◽  
Vol 50 (01) ◽  
pp. 1-16 ◽  
Author(s):  
Santosh Mhaske ◽  
Ranjeet Dhokale
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Total Synthesis ◽  
Scientific Community ◽  
Multicomponent Reactions ◽  
Polycyclic Aromatic Compounds ◽  
Polycyclic Aromatic ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

The plethora of transformations attainable by the transition-metal-catalyzed reactions of arynes has found immense contemporary interest in the scientific community. This review highlights the scope and importance of transition-metal-catalyzed aryne reactions in the field of synthetic organic chemistry reported to date. It covers transformations achieved by the combination of arynes and various transition metals, which provide a facile access to a biaryl motif, fused polycyclic aromatic compounds, different novel carbocycles, various heterocycles, and complex natural products.1 Introduction2 Insertion of Arynes3 Annulation of Arynes4 Cycloaddition of Arynes5 Multicomponent Reactions of Arynes6 Miscellaneous Reactions of Arynes7 Total Synthesis of Natural Products Using Arynes8 Conclusion

The Trost Synthesis of Bryostatin 16

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Total Synthesis ◽  
Anticancer Agent ◽  
Selective Reduction ◽  
Unsaturated Aldehyde ◽  
Stanford University ◽  
Structure Activity ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

In a showcase for the specific transition metal–catalyzed couplings that he has developed, including the elegant Ru-catalyzed coupling of 1 and 2, Barry M. Trost of Stanford University reported (Nature 2008, 456, 485; J. Am. Chem. Soc. 2010, 132, 16403) the total synthesis of the potent anticancer agent, bryostatin 16 4. The preparation of 1 began with commercial 2,2-dimethylpropanediol 5. Brown allylation of the aldehyde 6 followed by protection and oxidative cleavage delivered 8. Condensation (J. Am. Chem. Soc. 2000, 122, 11727) with 9 followed by selective reduction and Sn-catalyzed lactonization led to 10, which was carried on to the ketone 1. The aldehyde 6 was also the starting material for the preparation of 2. Addition of the anion 12 followed by hydrolysis established the unsaturated aldehyde, which was combined with 13 to give the racemic alcohol 14. Oxidation followed by Itsuno-Corey reduction then completed the synthesis of 2. What followed was a spectacular sequence of three transition metal–catalyzed transformations. Intermolecular Ru-mediated coupling of 1 with 2 delivered the tetrahydropyran 3. Pd catalysis effected the selective intramolecular coupling of the two alkynes of the derived ester 15, to give 16. The constrained alkynyl alcohol 16 cyclized under Au catalysis to give the dihydropyran 17, completing the construction of the skeleton of bryostatin 16 4. The route to the bryostatins outlined here is short enough (26 linear steps) and flexible enough to allow a thorough search of structure–activity relationships for this potent class of natural products.

scholarly journals Recent Advances in the Development of Catalytic Methods that Construct Medium-Ring Lactams, Partially Saturated Benzazepines and Their Derivatives

Synthesis ◽  
2021 ◽  
Author(s):  
Tom G. Driver ◽  
Wrickban Mazumdar
Keyword(s):  
Transition Metal ◽  
Multicomponent Reactions ◽  
Beckmann Rearrangement ◽  
Partially Saturated ◽  
Recent Advances ◽  
Transition Metal Catalyzed ◽  
Rearrangement Reactions ◽  
Catalyzed Reactions ◽  
Metal Catalyzed ◽  
Medium Ring

AbstractRecent catalytic methods to construct medium-sized lactams­ and partially saturated benzazepines and their derivatives are surveyed. The review is divided into the following sections:1 Introduction2 Non-Transition-Metal-Catalyzed Reactions2.1 Beckmann Rearrangement2.2 Non-Beckmann Rearrangement Reactions2.3 Multicomponent reactions3 Transition-Metal-Catalyzed Reactions3.1 Gold-Catalyzed Reactions to Access Medium-Sized N-Hetero­cycles3.2 Reactions Involving a Metal η3-Complex Catalytic Intermediate3.3 Transition-Metal-Catalyzed Reactions of Strained Cycloalkanes4 Conclusions

Transition Metal Catalyzed C-H bond Activation/Functionalization and Annulation of Phthalazinones

2021 ◽  
Author(s):  
Chandrasekaran Sivaraj ◽  
Alagumalai Ramkumar ◽  
Nagesh Sankaran ◽  
THIRUMANAVELAN GANDHI
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Bond Activation ◽  
Bioactive Molecules ◽  
Structural Motifs ◽  
The Past ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Phthalazinones and their higher congeners are commonly prevalent structural motifs that occur in natural products, bioactive molecules, and pharmaceuticals. In the past few decades transition metal-catalyzed reactions have received an...

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