Synthesis of macrocyclic lactams and lactones via ring-closing olefin metathesis

Goldring, William; Hodder, AndréS.; Weiler, Larry

doi:10.1016/s0040-4039(98)00966-6

Cited by 57 publications

(32 citation statements)

References 15 publications

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“…As shown by Reichwein and Liskamp [28,29], incorporation of N-alkenyl amino acids or proline residues will foster the efficiency of the cyclization reaction. Alternatively, reversible backbone protection by, among others, amide protection by either a 2,4-dimethoxybenzyl functionality [80] or tert-butyloxycarbonyl group [81] or by incorporation of pseudoprolines [82] is a versatile approach to overcome these difficulties during RCM-mediated cyclization reactions [79]. Schmiedeberg and Kessler [79] synthesized a series of uPA-derived peptides (general template, 65) in which , were substituted by the racemic amino acids…”

Section: Stabilization Of α-Helices and β-Turns In Peptidesmentioning

confidence: 99%

Synthesis of Cyclic Peptides and Peptidomimetics by Metathesis Reactions

Rijkers

2015

Topics in Heterocyclic Chemistry

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This review surveys developments in the field of ring-closing metathesis and cross-metathesis reactions applied to the synthesis of constrained amino acids, peptides, and peptidomimetics. Examples, in which metathesis is used as one of the synthetic tools to arrive at the desired peptide molecules as well as examples that describe in-depth optimized metathesis protocols, will be discussed. Currently, metathesis reactions are well-accepted synthetic tools within the field of peptide chemistry and provide peptides unprecedented properties like conformational, metabolic, and chemical stability and improved bioactivity.

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Section: Stabilization Of α-Helices and β-Turns In Peptidesmentioning

confidence: 99%

Synthesis of Cyclic Peptides and Peptidomimetics by Metathesis Reactions

Rijkers

2015

Topics in Heterocyclic Chemistry

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“…In larger rings, the conformational impact of functionalization is often unpredictable, particularly as the molecular complexity increases. Even the position of the double bonds relative to ancillary functional groups can have a profound impact [94,95]. In RCM to form the gleosporone framework, for example, the macrolactone could be formed only after inserting an additional methylene group on the "ether" side of the ester unit: this outcome was attributed to gearing effects, but could not be predicted a priori [73].…”

Section: Substituent-induced Conformational Constraintsmentioning

confidence: 99%

Ring-Closing Metathesis Synthesis of Medium and Large Rings: Challenges and Implications for Sustainable Synthesis

Monfette

Fogg

2010

Green Metathesis Chemistry

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Synthesis of medium-sized and macrocyclic rings by ring closing metathesis (RCM) reactions of dienes involves challenges not found in synthesis of the more common five-and six-membered rings. This review discusses factors that determine the probability and efficiency of cyclization, and experimental methods that have been used to increase selectivity for RCM products, with specific reference to the concentrations at which RCM can be achieved. These issues have important implications for the environmental and economic sustainability of large-scale synthetic processes utilizing RCM for assembly of rings larger than six members.

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“…Contudo, se a quelação das espécies intermediárias for muito estável, a reação pode ter sua evolução impedida. Em estudos sistemáticos de formação de macrolactonas (18, X = O) e macrolactamas (18, X = NH ou NBoc) de 14 membros via RCM, a partir dos dienos 17 em presença do catalisador de rutênio 3, Weiler e colaboradores mostraram que a proximidade das ligações dupla a grupos polares (oxigênio da carbonila ou oxigênio/nitrogênio do anel) reduz drasticamente o rendimento da ciclização (Esquema 5) 38 .…”

Section: Papel Dos Grupos Polaresunclassified

Metátese de olefinas aplicada ao fechamento de anéis: uma ferramenta poderosa para a síntese de macrociclos naturais

Santos¹,

Kaiser²,

Férézou³

2008

Quím. Nova

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Recebido em 7/3/07; aceito em 30/8/07; publicado na web em 26/2/08 RING-CLOSING OLEFIN METATHESIS: A POWERFUL TOOL FOR THE SYNTHESIS OF NATURAL MACROCYCLES. For a quarter of a century, metathesis has become indispensable for the synthesis of natural and non-natural products, particularly of biologically active compounds. This review illustrates through a maximum of appropriate examples the power and the versatility of the metathesis ring-closure (RCM) reaction as a key ring-closure methodology for the synthesis of natural macrocycles. Its high functional group compatibility as well as the possibility of further transformations makes this reaction a powerful tool in the cases where the structural framework and function requirements are difficult to meet.

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Synthesis of macrocyclic lactams and lactones via ring-closing olefin metathesis

Cited by 57 publications

References 15 publications

Synthesis of Cyclic Peptides and Peptidomimetics by Metathesis Reactions

Synthesis of Cyclic Peptides and Peptidomimetics by Metathesis Reactions

Ring-Closing Metathesis Synthesis of Medium and Large Rings: Challenges and Implications for Sustainable Synthesis

Metátese de olefinas aplicada ao fechamento de anéis: uma ferramenta poderosa para a síntese de macrociclos naturais

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