Ruthenium-Catalyzed Metathesis Cascade Reactions in Natural Products Synthesis

Han, Jing‐Chun; Li, Chuang‐Chuang

doi:10.1002/tcr.201600110

Cited by 8 publications

(4 citation statements)

References 161 publications

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“…7 The cyclization reaction utilized ruthenium-catalyzed ring-closing olefin metathesis (RCM), affording cis and trans olefin analogues of enkephalins, which resulted in metabolic stability and rigid conformation. 8 Despite the amount of literature reporting the use of RCM in peptide chemistry, 9 and a great variety of enkephalin derivatives, 10 this cyclization strategy has not yet been proven on bivalent analogues such as biphalin. Biphalin is an octapeptide characterized by two enkephalin-derived pharmacophores joined together by a hydrazine bridge; biphalin is able to bind μand δ-opioid receptors with an EC 50 of 1−5 nM, with a strong antinociceptive effect associated with few side-effects and low dependence upon chronic use.…”

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confidence: 99%

Novel Cyclic Biphalin Analogues by Ruthenium-Catalyzed Ring Closing Metathesis: in Vivo and in Vitro Biological Profile

Stefanucci

Pieretti

et al. 2019

ACS Med. Chem. Lett.

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In this work we report the application of the ring-closing metathesis (RCM) to the preparation of two cyclic olefin-bridged analogues of biphalin (Tyr-D-Ala-Gly-Phe-NH-NH ← Phe ← Gly ← D-Ala ← Tyr), using the second generation Grubbs' catalyst. The resulting cis-and trans-cyclic isomers were identified, fully characterized, and tested in vitro at μ (ΜΟR), δ (DOR), and κ (KOR) opioid receptors and in vivo for antinociceptive activity. Both were shown to be full agonists at MOR and potential partial antagonists at DOR, with low potency KOR agonism. They also share a strong antinociceptive effect after intracerebroventricular (i.c.v.) and intravenous (i.v.) administration, higher than that of the cyclic biphalin analogues containing a disulfide bridge between the side chains of two D-Cys or D-Pen residues, previously described by our group.

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confidence: 99%

Novel Cyclic Biphalin Analogues by Ruthenium-Catalyzed Ring Closing Metathesis: in Vivo and in Vitro Biological Profile

Stefanucci

Pieretti

et al. 2019

ACS Med. Chem. Lett.

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“…Since the pioneering work of Grubbs describing ruthenium‐catalyzed metathesis cascade reactions, [102] a few variants of metathesis reactions have been developed and efficiently applied in the field of total synthesis of natural products [103] . In this regard, metathesis reactions have become, since their discovery, some the most important strategies for the carbon‐carbon bond formation, with the ring‐closing metathesis (RCM) being an excellent strategy in modern organic synthetic chemistry.…”

Section: Cycloaddition Reactionsmentioning

confidence: 99%

Fluorinated Imines in Tandem and Cycloaddition Reactions

Escorihuela

Fustero

2023

The Chemical Record

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The chemistry of fluorinated compounds has experienced extraordinary growth in recent decades due to the many and varied properties which many of the compounds that contain fluorinated groups possess. Among all of them, fluorinated chiral imines, in particular the Ellman's imines, are of great importance since they are some of the most interesting building blocks for the synthesis of a large number of enantioenriched carbocycles and heterocycles with extraordinary biological and synthetic properties. This personal account covers the most significant results obtained in our research group in the last two decades concerning asymmetric tandem reactions, paying special attention to the intramolecular aza‐Michael reaction (IMAMR), diversity oriented synthesis (DOS), asymmetric tandem reactions involving a p‐tolylsulfinyl group as chiral inducer and cycloaddition processes, in particular, the Pauson‐Khand reaction, [2+2+2]‐cycloadditions and metathesis reactions, starting mainly from enyne compounds and through the use of fluorinated chiral N‐sulfinyl imines and their derivatives as starting materials.

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“…Transition metal-mediated cascade reactions have been extensively explored in small molecule and natural product synthesis. [43][44][45][46][47] Several of these reactions have been successfully applied to cascade polymerizations. Double cyclization polymerizations, [48][49][50] and various combinations of cyclopolymerization with chain walking (typically with Pd or Ni catalysts) [51][52][53] have already been extensively reviewed in the literature.…”

Section: Metathesis Cascade Polymerizationsmentioning

confidence: 99%