Diaryl Ether Formation in the Synthesis of Natural Products

Pitsinos, Emmanuel N.; Vidali, Veroniki P.; Couladouros, Elias A.

doi:10.1002/ejoc.201001520

Cited by 145 publications

(75 citation statements)

References 198 publications

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“…The most logical approach to the synthesis of 1 would be to start with the preparation of a diaryl ether. This functionality is present in many important bioactive natural compounds [19] and it is not surprising that a great amount of effort has been focused on the development and improvement of the methods to form diaryl ethers [20–21]. The Ullman reaction is often used to prepare diaryl ethers, but this reaction has the disadvantages of high reaction temperatures and intolerance to a wide variety of functional groups, with the major weakness being the inconsistency in the products obtained by the use of different copper sources [22–24].…”

Section: Resultsmentioning

confidence: 99%

Total synthesis of ochnaflavone

Ndoile

Heerden

2013

Beilstein J. Org. Chem.

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SummaryThe first total syntheses of ochnaflavone, an asymmetric biflavone consisting of apigenin and luteolin moieties, and the permethyl ether of 2,3,2'',3''-tetrahydroochnaflavone have been achieved. The key steps in the synthesis of ochnaflavone were the formation of a diaryl ether and ring cyclization of an ether-linked dimeric chalcone to assemble the two flavone nuclei. Optimal experimental conditions for the oxidative cyclization to form ochnaflavone were established.

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Section: Resultsmentioning

confidence: 99%

Total synthesis of ochnaflavone

Ndoile

Heerden

2013

Beilstein J. Org. Chem.

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“…Specifically, given the prevalence of the biaryl ether moiety as a ''privileged structure'' in bioactive natural products, for example vancomycin, teicoplanin, piperazinomycin and others, 74,75 it is not surprising that methods for ring closure to form this functionality have seen wide application. In particular, the ease and effectiveness of such S N Ar processes on solid support make it attractive for the synthesis of peptidomimetics containing a biaryl ether and related moieties.…”

Section: Nucleophilic Aromatic Substitution (S N Ar)mentioning

confidence: 98%

The Synthesis of Macrocycles for Drug Discovery

Peterson¹

2014

Macrocycles in Drug Discovery

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Despite the attractive nature of macrocyclic compounds for use in new pharmaceutical discovery, applications have been hindered due to the lack of appropriate synthetic methods, in particular for the construction of libraries of such molecules. However, over the last decade, a number of effective and versatile methodologies suitable for macrocyclic scaffolds have been developed and applied successfully. These include classical coupling and substitution reactions, ring-closing metathesis (RCM), cycloaddition (“click”) chemistry, multicomponent reactions (MCR), numerous organometallic-mediated processes and others. This chapter presents a comprehensive compilation of these strategies and provides examples of their use in drug discovery, along with a description of those approaches that have proven effective for the assembly of macrocyclic libraries suitable for screening.

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“…The authors reported higher yields and shorter reaction times compared with conventional heating and sealed tubes. These macrocyclic diaryl ethers are commonly found in natural compounds ( Figure 12) and have been reported to mediate a broad range of biological activities [94][95][96]. The buflavine derivatives encompassing a 8-membered cycle 246, were obtained by allylation of biaryls 244 and subsequent RCM using Grubb's II catalyst.…”

Section: Mw-assisted Syntheses Of Macrocyclic Natural Products and Anmentioning

confidence: 99%

Microwave-Assisted Syntheses of Bioactive Seven-Membered, Macro-Sized Heterocycles and Their Fused Derivatives

et al. 2016

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This review describes the recent advances in the microwave-assisted synthesis of 7-membered and larger heterocyclic compounds. Several types of reaction for the cyclization step are discussed: Ring Closing Metathesis (RCM), Heck and Sonogashira reactions, Suzuki-Miyaura cross-coupling, dipolar cycloadditions, multi-component reactions (Ugi, Passerini), etc. Green syntheses and solvent-free procedures have been introduced whenever possible. The syntheses discussed herein have been selected to illustrate the huge potential of microwave in the synthesis of highly functionalized molecules with potential therapeutic applications, in high yields, enhanced reaction rates and increased chemoselectivity, compared to conventional methods. More than 100 references from the recent literature are listed in this review.

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Diaryl Ether Formation in the Synthesis of Natural Products

Cited by 145 publications

References 198 publications

Total synthesis of ochnaflavone

Total synthesis of ochnaflavone

The Synthesis of Macrocycles for Drug Discovery

Microwave-Assisted Syntheses of Bioactive Seven-Membered, Macro-Sized Heterocycles and Their Fused Derivatives

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