Synthesis of Diaminosuberic Acid Derivatives via Ring-Closing Alkyne Metathesis

Aguilera, Begoña; Wolf, Larissa B.; Nieczypor, Piotr; Rutjes, Floris P. J. T.; Overkleeft, Hermen S.; Hest, Jan C. M. van; Schoemaker, Hans E.; Wang, Bing; Mol, J.C.; Fürstner, Alois; Overhand, Mark; Marel, Gijsbert A. van der; Boom, Jacques H. van

doi:10.1021/jo001734x

Cited by 64 publications

(31 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[71] As shown in Scheme 14, the orthogonally protected adduct 53 was prepared from 52 in four steps. Tungsten alkylidyne 9 mediated cyclization of 53 provided cyclic alkyne 54 in 66 % yield.…”

Section: Ring-closing Alkyne Metathesis (Rcam)mentioning

confidence: 99%

Alkyne Metathesis: Catalysts and Synthetic Applications

2007

View full text Add to dashboard Cite

There has been rapid progress and growing interest in alkyne metathesis within the past decade. The availability of highly active catalysts as well as their applications in both organic synthesis and polymer chemistry has served to motivate the advancement of this field. In this article, the development of several different metathesis catalysts, including two heterogeneous ones, are reviewed with an emphasis on comparing strengths and weaknesses. In Section 4, the applications of alkyne metathesis to synthesis of natural products, conjugated polymers as well as shape-persistent macrocycles are discussed. In the last section, a comparison of alkyne metathesis to the well established alkene metathesis is given. Developing an alkyne metathesis catalyst with both high reactivity and robustness to air and moisture remains an unsolved problem of this important and useful reaction.

show abstract

Section: Ring-closing Alkyne Metathesis (Rcam)mentioning

confidence: 99%

Alkyne Metathesis: Catalysts and Synthetic Applications

2007

View full text Add to dashboard Cite

show abstract

“…[6][7][8][9] In developing such ligands, truncated peptide analogues are becoming increasingly popular. For example, [Nle 30 ]hPP [25][26][27][28][29][30][31][32][33][34][35][36] and [Leu 34 ]pNPY [25][26][27][28][29][30][31][32][33][34][35][36] were found to be Y 4 R selective partial agonists, 10 and a nonapeptide based on the C-terminal fragment of NPY, Ile-Asn-Pro-Ile-Tyr-Arg-Leu-Arg- [28][29][30][31][32][33][34][35][36] ], also known as 1229U91, showed enhanced potency at both receptor subtypes but is in particular the most potent known Y 1 R antagonist. [13][14][15][16][17] Another of several highly potent Y receptor ligands based upon dimeric C-terminal sequences is D/L-2,7-diaminooctanedioyl-bis(YRLRY-NH 2 ), 1 (BVD-74D) 18 ( …”

Section: Introductionmentioning

confidence: 99%

Optically Pure, Structural, and Fluorescent Analogues of a Dimeric Y₄ Receptor Agonist Derived by an Olefin Metathesis Approach

et al. 2016

View full text Add to dashboard Cite

(2016) Optically pure, structural and fluorescent analogues of a dimeric Y4 receptor agonist derived by an olefin metathesis approach. Journal of Medicinal Chemistry . ISSN 1520-4804 Access from the University of Nottingham repository: http://eprints.nottingham.ac.uk/34144/1/acs.jmedchem.6b00310.pdf Copyright and reuse:The Nottingham ePrints service makes this work by researchers of the University of Nottingham available open access under the following conditions. This article is made available under the University of Nottingham End User licence and may be reused according to the conditions of the licence. For more details see: http://eprints.nottingham.ac.uk/end_user_agreement.pdf A note on versions:The version presented here may differ from the published version or from the version of record. If you wish to cite this item you are advised to consult the publisher's version. Please see the repository url above for details on accessing the published version and note that access may require a subscription.For more information, please contact eprints@nottingham.ac.uk Just Accepted "Just Accepted" manuscripts have been peer-reviewed and accepted for publication. They are posted online prior to technical editing, formatting for publication and author proofing. The American Chemical Society provides "Just Accepted" as a free service to the research community to expedite the dissemination of scientific material as soon as possible after acceptance. "Just Accepted" manuscripts appear in full in PDF format accompanied by an HTML abstract. "Just Accepted" manuscripts have been fully peer reviewed, but should not be considered the official version of record. They are accessible to all readers and citable by the Digital Object Identifier (DOI®). "Just Accepted" is an optional service offered to authors. Therefore, the "Just Accepted" Web site may not include all articles that will be published in the journal. After a manuscript is technically edited and formatted, it will be removed from the "Just Accepted" Web site and published as an ASAP article. Note that technical editing may introduce minor changes to the manuscript text and/or graphics which could affect content, and all legal disclaimers and ethical guidelines that apply to the journal pertain. ACS cannot be held responsible for errors or consequences arising from the use of information contained in these "Just Accepted" manuscripts. 1Optically pure, structural and fluorescent analogues of a dimeric Y 4 receptor agonist derived by an olefin metathesis approach. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59

show abstract

“…[58] Though much less established, the metathesis of alkynes in general, and the only recently discovered ring-closing metathesis of diynes (RCAM) [34] in particular, also hold great promise for target-oriented synthesis, not least because of the exceedingly high tolerance of the available catalysts. The approach to sophorolipid lactone, together with several other applications from this laboratory, [59,60] bear witness to this notion and may encourage more extensive uses of this versatile methodology in advanced organic synthesis.…”

Section: Discussionmentioning

confidence: 99%

Total Syntheses and Biological Assessment of Macrocyclic Glycolipids

Fürstner

2004

Eur J Org Chem

Self Cite

View full text Add to dashboard Cite

Novel strategies for the synthesis of structurally complex macrocyclic glycolipids are outlined which have opened concise and highly flexible entries into various resin glycosides and sugar-based macrodiolides. The key design elements consist of either a ring-closing alkene (RCM) or alkyne metathesis (RCAM) event or a newly developed template-directed dilactonization reaction. The performance and excellent application profile of these transformations are illustrated by the total syntheses of tricolorin A and G, woodrosin I, sophorolipid lactone, cycloviracin B₁, glucolipsin A, and various analogues thereof. A brief survey of the biological activities exerted by these amphiphilic natural products is provided

show abstract

Synthesis of Diaminosuberic Acid Derivatives via Ring-Closing Alkyne Metathesis

Cited by 64 publications

References 18 publications

Alkyne Metathesis: Catalysts and Synthetic Applications

Alkyne Metathesis: Catalysts and Synthetic Applications

Optically Pure, Structural, and Fluorescent Analogues of a Dimeric Y₄ Receptor Agonist Derived by an Olefin Metathesis Approach

Total Syntheses and Biological Assessment of Macrocyclic Glycolipids

Contact Info

Product

Resources

About

Synthesis of Diaminosuberic Acid Derivatives via Ring-Closing Alkyne Metathesis

Cited by 64 publications

References 18 publications

Alkyne Metathesis: Catalysts and Synthetic Applications

Alkyne Metathesis: Catalysts and Synthetic Applications

Optically Pure, Structural, and Fluorescent Analogues of a Dimeric Y4 Receptor Agonist Derived by an Olefin Metathesis Approach

Total Syntheses and Biological Assessment of Macrocyclic Glycolipids

Contact Info

Product

Resources

About

Optically Pure, Structural, and Fluorescent Analogues of a Dimeric Y₄ Receptor Agonist Derived by an Olefin Metathesis Approach