Aryne-Based Multicomponent Coupling Reactions

Synlett ◽  
2020 ◽  
Vol 31 (08) ◽  
pp. 750-771
Author(s):  
Daesung Lee ◽  
Sourav Ghorai
Keyword(s):  
Multicomponent Reactions ◽  
Chemical Space ◽  
Alder Reaction ◽  
Diels Alder ◽  
Coupling Reactions ◽  
Fused Heterocycles ◽  
Diels Alder Reaction ◽  
Multicomponent Coupling Reactions ◽  
Metal Catalyzed ◽  
Multicomponent Coupling

Multicomponent reactions (MCRs) constitute a powerful synthetic tool to generate a large number of small molecules with high atom economy, which thus can efficiently expand the chemical space with molecular diversity and complexity. Aryne-based MCRs offer versatile possibilities to construct functionalized arenes and benzo-fused heterocycles. Because of their electrophilic nature, arynes couple with a broad range of nucleophiles. Thus, a variety of aryne-based MCRs have been developed, the representative of which are summarized in this account.1 Introduction2 Aryne-Based Multicomponent Reactions2.1 Trapping with Isocyanides2.2 Trapping with Imines2.3 Trapping with Amines2.4 Insertion into π-Bonds2.5 Trapping with Ethers and Thioethers2.6 Trapping with Carbanions2.7 Transition-Metal-Catalyzed Approaches3 Strategies Based on Hexadehydro Diels–Alder Reaction3.1 Dihalogenation3.2 Halohydroxylation and Haloacylation3.3 Amides and Imides3.4 Quinazolines3.5 Benzocyclobutene-1,2-diimines and 3H-Indole-3-imines3.6 Other MCRs of Arynes and Isocyanides4 Conclusion

scholarly journals Studies on the transannular Diels–Alder reaction of 15-membered macrocyclic trienes containing a trans-trans diene. Part I: Synthesis and isomerization of various model cyclopentadecatrienes

1995 ◽  
Vol 73 (10) ◽  
pp. 1675-1694 ◽  
Author(s):  
Dennis G. Hall ◽  
Renate Müller ◽  
Pierre Deslongchamps
Keyword(s):  
Aqueous Media ◽  
Alder Reaction ◽  
Membered Ring ◽  
Diels Alder ◽  
Coupling Reactions ◽  
Diels Alder Reaction ◽  
Trans Diene

The transannular Diels–Alder reaction of 15-membered macrocyclic trienes with a trans-trans-cis (TTC) olefin geometry can lead to A.B.C.[6.6.7] tricyclic products of trans-syn-trans (TST) and cis-syn-cis (CSC) stereochemistry whereas the TTT isomers can produce the trans-anti-cis (TAC) and cis-anti-trans (CAT) tricycles. In order to study the influence of the position (pro-6.6 or pro-6.7) and the nature (alkyl, alkoxymethyl, or formyl) of the dienophile substituent, a set of 10 model cyclopentadecatrienes was prepared. The synthesis of appropriately functionalized trisubstituted dienophile and diene synthons, as well as their coupling reactions affording acyclic precursors, is described in this paper (first in a series of two). A mild and efficient macrocyclization protocol yielded the required methyl- or alkoxymethyl-substituted cyclic substrates. Further transformations led to the formyl-substituted ones. In particular, the TTT macrocycles containing an enal as a dienophile could be completely isomerized to the corresponding TTC thermodynamic isomers in acidic aqueous media. Keywords: transannular, Diels–Alder, 15-membered ring, A.B.C.[6.6.7] tricycles, diterpene.

Transition-metal-catalyzed multicomponent coupling reactions with imines and carbon monoxide

2013 ◽  
Vol 85 (2) ◽  
pp. 377-384 ◽  
Author(s):  
Jeffrey S. Quesnel ◽  
Bruce A. Arndtsen
Keyword(s):  
Transition Metal ◽  
Building Blocks ◽  
Coupling Reactions ◽  
Metal Catalysis ◽  
Heterocyclic Derivatives ◽  
One Step ◽  
Multicomponent Coupling Reactions ◽  
Metal Catalyzed ◽  
And Control ◽  
Multicomponent Coupling

Multicomponent coupling reactions provide a method to combine several substrates in a single reaction. When coupled with transition-metal catalysis, these reactions can be used to both activate and control the assembly of multiple simple building blocks directly into useful products. This account will describe our work in this area, with a focus on the use of palladium catalysis as a tool to couple imines and CO with other substrates into a range of heterocyclic derivatives in one-step reactions.

Recent progress in the synthesis of bioactive polycyclic natural products

2007 ◽  
Vol 79 (4) ◽  
pp. 651-665 ◽  
Author(s):  
Masaaki Miyashita
Keyword(s):  
Chemical Synthesis ◽  
Stereoselective Synthesis ◽  
Leukemia Cell ◽  
Alder Reaction ◽  
Diels Alder ◽  
Coupling Reactions ◽  
Chemical Structures ◽  
Ovariectomized Mice ◽  
Diels Alder Reaction ◽  
Zoanthamine Alkaloids

The zoanthamine alkaloids, a type of heptacyclic marine alkaloid isolated from colonial zoanthids of the genus Zoanthus sp., have distinctive biological and pharmacological properties as well as their unique chemical structures with stereochemical complexity. Namely, norzoanthamine can suppress the loss of bone weight and strength in ovariectomized mice and has been considered a promising candidate for an antiosteoporotic drug, whereas zoanthamine has exhibited potent inhibitory activity toward phorbol myristate-induced inflammation in addition to powerful analgesic effects. Recently, norzoanthamine derivatives were demonstrated to inhibit strongly the growth of P-388 murine leukemia cell lines, in addition to their potent antiplatelet activities on human platelet aggregation. These distinctive biological properties, combined with novel chemical structures, make this family of alkaloids extremely attractive targets for chemical synthesis. However, the chemical synthesis of the zoanthamine alkaloids has been impeded owing to their densely fuctionalized complex stereostructures. We report here the first and highly stereoselective total syntheses of norzoanthamine and zoanthamine, which involves stereoselective synthesis of the requisite triene for intramolecular Diels-Alder reaction via three-component coupling reactions, a key intramolecular Diels-Alder reaction, and subsequent crucial bis-aminoacetalization as the key steps.

Diels–Alder Reactions of 1,2-Dihydropyridines: An Efficient Tool for the Synthesis of Isoquinuclidines

Synthesis ◽  
2018 ◽  
Vol 50 (09) ◽  
pp. 1773-1782 ◽  
Author(s):  
Eduarda Silva ◽  
Artur Silva ◽  
Djenisa Rocha
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Efficient Tool ◽  
Organometallic Catalysts ◽  
Diels Alder Reaction ◽  
Straightforward Method ◽  
Recent Developments ◽  
Catalyzed Reactions ◽  
Metal Catalyzed ◽  
Valuable Compounds

The Diels–Alder reaction of 1,2-dihydropyridines with different dienophiles is a well-established and straightforward method for the synthesis of isoquinuclidines. Nevertheless, the enantioselective preparation of isoquinuclidines using organocatalysts or organometallic catalysts is rather unexplored. This succinct review offers readers an overall perspective of the most important recent developments and concepts related to this topic.1 Introduction2 Asymmetric Diels–Alder Reaction of 1,2-Dihydropyridines2.1 Transition-Metal-Catalyzed Reactions2.2 Organocatalyzed Reactions3 Diels–Alder Reaction of 1,2-Dihydropyridines in the Synthesis of Biologically Valuable Compounds4 Conclusion

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