Short and Efficient Approach Towards Macrocyclic Lactones Based on a Sonogashira Reaction

Krauß, Jürgen; Unterreitmeier, Doris; Neudert, Christine; Bracher, Franz

doi:10.1002/ardp.200500132

Cited by 13 publications

(10 citation statements)

References 8 publications

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“…217 Lastly, simple macrolactones have been synthesized using primarily Sonogashira coupling for ring closure. 218 …”

Section: Sonogashiramentioning

confidence: 99%

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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“…217 Lastly, simple macrolactones have been synthesized using primarily Sonogashira coupling for ring closure. 218 …”

Section: Sonogashiramentioning

confidence: 99%

The Synthesis of Macrocycles for Drug Discovery

Peterson¹

2014

Macrocycles in Drug Discovery

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“…The residue was purified by FCC (n-hexane/ethyl acetate 20 : 1) to give 820 mg (90%) of 3a as a colorless oil. 1 1-Furan-2-ylpent-4-en-1-yl undedec-10-enoate 3b…”

Section: -Furan-2-ylbut-3-en-1-yl Undec-10-enoate 3amentioning

confidence: 99%

“…The compound was prepared in the same manner as described for 3a from 510 mg (3.1 mmol) 1-furan-2-ylhex-5-en-1-ol 2c and 620 mg (3.1 mmol) undec-10-enoylchloride to give 370 mg (36%) of 3b as a colorless oil. 1 (Z)-15-Furan-2-yl-oxacyclopentadec-11-en-2-one 4b…”

Section: -Furan-2-ylhex-5-en-1-yl Undec-10-enoate 3cmentioning

confidence: 99%

“…Toluene was used as solvent instead of DCM. The reaction time was 10 h. 1 (Z)-16-Furan-2-yl-1-oxacyclohexadec-11-en-2-one 4c…”

Section: -Furan-2-ylhex-5-en-1-yl Undec-10-enoate 3cmentioning

confidence: 99%

“…In continuation of our work on cytotoxic furan compounds [1,2] we tried to find out, whether unsaturated furyl macrolactones show cytotoxic activities. Furan and tetrahydrofuran heterocycles are part of numerous natural cytotoxic products like (l)-4-ipomeanol 1a [3], furano-epothilone D 1b [4] (Fig.…”

Section: Introductionmentioning

confidence: 99%

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New Approach towards Cytotoxic Furyl Macrolactones by Ring Closing Metathesis

Krauss¹,

Bracher²,

Unterreitmeier³

2006

Archiv der Pharmazie

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Furan-2-ylalkenols 2a-d were esterified with undec-10-enoyl chloride and the resulting esters were cyclized to unsaturated 2- and 3-furyl macrolactones by ring closing metathesis using Grubbs catalyst I. Hydrolysis of the macrolactone 4b with NaOH led to the furylalkenoic acid and reaction of 4c with tert-butyllithium gave a tert-butyl ketone. Some of the resulting compounds were tested in the MTT assay for their cytotoxic activities against HL 60 cells and at the National Cancer Institute (NCI) against 60 cancer cell lines. The compounds only showed cytotoxic activities in the muM range.

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Sonogashira Coupling

2010

Comprehensive Organic Name Reactions and Reagents

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It is a palladium‐catalyzed noncarbonylative coupling between terminal acetylenes (alkynes) and aryl or vinyl halides in the presence of a copper (I) salt and a large excess of amine (as the solvent or co‐solvent). Therefore, this reaction is generally known as the Sonogashira coupling. Occasionally, this reaction is also referred to as the Sonogashira–Hagihara reaction. The reaction's conditions, mechanistic features and weaknesses of the Sonogashira coupling have been discussed. The most important improvement for the Sonogashira coupling is probably to perform this reaction under copper‐free conditions. This reaction has very broad application in the preparation of alkynes.

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Short and Efficient Approach Towards Macrocyclic Lactones Based on a Sonogashira Reaction

Cited by 13 publications

References 8 publications

The Synthesis of Macrocycles for Drug Discovery

The Synthesis of Macrocycles for Drug Discovery

New Approach towards Cytotoxic Furyl Macrolactones by Ring Closing Metathesis

Sonogashira Coupling

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