A synthetic route to enediyne-bridged amino acids

Jerić, Ivanka; Chen, Hueih-Min

doi:10.1016/j.tetlet.2007.05.016

Cited by 10 publications

(6 citation statements)

References 17 publications

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“…Jeric and co‐workers introduced a general strategy for the preparation of enediyne–amino acid conjugates such as

bold19

. Their study showed that peptide‐based enediynes can undergo Bergman cyclization at relative low temperatures where H‐bonding between the terminal groups may play a role.…”

Section: The Chemistry Of Enediynes and Related Compoundsmentioning

confidence: 99%

Enediynes, enyne‐allenes, their reactions, and beyond

Kraka

2013

WIREs Comput Mol Sci

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Enediynes undergo a Bergman cyclization reaction to form the labile 1,4-didehydrobenzene (p-benzyne) biradical. The energetics of this reaction and the related Schreiner-Pascal reaction as well as that of the Myers-Saito and Schmittel reactions of enyne-allenes are discussed on the basis of a variety of quantum chemical and available experimental results. The computational investigation of enediynes has been beneficial for both experimentalists and theoreticians because it has led to new synthetic challenges and new computational methodologies. The accurate description of biradicals has been one of the results of this mutual fertilization. Other results have been the computer-assisted drug design of new antitumor antibiotics based on the biological activity of natural enediynes, the investigation of hetero-and metallo-enediynes, the use of enediynes in chemical synthesis and materials science, or an understanding of catalyzed enediyne reactions. C 2013 John

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“…Jeric and co‐workers introduced a general strategy for the preparation of enediyne–amino acid conjugates such as

bold19

. Their study showed that peptide‐based enediynes can undergo Bergman cyclization at relative low temperatures where H‐bonding between the terminal groups may play a role.…”

Section: The Chemistry Of Enediynes and Related Compoundsmentioning

confidence: 99%

Enediynes, enyne‐allenes, their reactions, and beyond

Kraka

2013

WIREs Comput Mol Sci

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“…125,130 In 2007, the enediyne-bridged amino acid 223 was synthesized via a low-yielding route in which the first step was the reaction of alkyne 219 with 2 equiv of 1 in Et 2 NH at room temperature in the presence of 10 mol% PdCl 2 (PPh 3 ) 2 and 10 mol% CuI, which provided the (Z)chloroenyne derivative of lysine 220 in 47% yield (Scheme 77). 131…”

Section: Excellent Site Selectivity Was Unexpectedly Observed Bymentioning

confidence: 99%

Development and applications of highly selective palladium-catalyzed monocoupling reactions of (cyclo)alkenes and 1,3-alkadienes bearing two or three electrophilic sites and bis(enol triflates) with terminal alkynes

et al. 2013

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The motivation for writing this review with 558 references, which covers the literature up to the end of September 2012, is to fill a part of this gap by illustrating highly selective Pd/Cu-catalyzed and Cu-free Pd-catalyzed monoalkynylation reactions of (cyclo)alkenes and 1,3-butadienes bearing two or three identical or different electrophilic sites and bis(enol triflates) with terminal alkynes. However, Pd-catalyzed selective monocoupling reactions of 1-alkynes with (hetero)aryl halides or pseudohalides with two identical or different electrophilic sites will not be covered. Moreover, Pd-catalyzed monocoupling reactions of 1-alkynes with non-conjugated diene systems bearing an electrophilic site on each carbon–carbon double bond have also been considered to be beyond the scope of this review.\ud \ud In addition to describing and commenting on the aforementioned monoalkynylation reactions of (cyclo)alkenes and 1,3-dienes with two or three identical or different electrophilic sites and bis(enol triflates), emphasis has been placed on the use of Pd-catalyzed monoalkynylations of (cyclo)alkenes and 1,3-butadienes bearing two or three identical or different electrophilic sites and bis(enol triflates) as key steps of the syntheses of core structures and models of enediyne antitumor antibiotics, pharmacologically active compounds, and bioactive naturally occurring compounds including insect sex pheromone components, and fungal and plant metabolites. Moreover, the review has been focused on the formation of disubstituted acetylenic derivatives by one-pot site-selective Pd-catalyzed consecutive alkynylation reactions of di(pseudo)halogenated olefinic substrates with two different terminal alkynes. Where appropriate, the reasons for the observed stereo-, site-, and/or chemoselectivities of the reported Sonogashira-type monoalkynylation reactions have been mentioned and discussed

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“…Recently, Jeric et al [68] reported the first example of a enediyne-linked dipeptide 55. BC of these compounds was studied using CHD as the H-atom donor.…”

Section: 2mentioning

confidence: 99%

Recent Developments in Enediyne Chemistry

Joshi

Rawat

2012

Chemistry & Biodiversity

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The enediynes are known for highly potent anticancer, antimicrobial, as well as cytotoxic activities. The discovery of enediynes from natural sources was achieved in late 1980s. They are presently of high interest, because they exert their biological action due to their ability to form a diradical, which abstracts H-atoms from the DNA backbone, thus causing cell death. Nowadays, the major works are dedicated to the syntheses of enediynes. This review covers recent developments in enediyne chemistry of the last few decades. It is subdivided in six chapters dealing with the discussion of the chemistry and biological significances of enediynes, and the factors responsible for a better activation of enediynes and potent biological evaluations.

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A synthetic route to enediyne-bridged amino acids

Cited by 10 publications

References 17 publications

Enediynes, enyne‐allenes, their reactions, and beyond

Enediynes, enyne‐allenes, their reactions, and beyond

Development and applications of highly selective palladium-catalyzed monocoupling reactions of (cyclo)alkenes and 1,3-alkadienes bearing two or three electrophilic sites and bis(enol triflates) with terminal alkynes

Recent Developments in Enediyne Chemistry

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