Synthesis of methyl (5Z,8Z,10E,12E,14Z)-eicosapentaenoate

Mohamed, Yasser Mahmoud A.; Hansen, Trond Vidar

doi:10.1016/j.tetlet.2010.12.078

Cited by 33 publications

(26 citation statements)

References 26 publications

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“…17,18 A Z-stereoselective semireduction of triyne 7, was carried out via a modified Boland protocol using Zn(Cu/Ag) in presence of trimethylsilyl chloride (TMSCl) 19,20 at room temperature, to produce compound 6b in 65% yield. The modified Boland protocol, using Zn(Cu/Ag) in presence of TMSCl, proved to be important for this reaction 12,[20][21][22][23] (Scheme 1); the same reduction carried out with a Lindlar catalyst resulted in a complex mixture of products. 24 © ARKAT USA, Inc Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

“…From these results, we decided to investigate a mild and more efficient procedure for the hydrolysis of the methyl ester of the thiophene analogue 6b, as well as methyl bosseopentaenoate 5b that was prepared according to the reported literature procedures. 12 Herein, an in situ formation of LiI in a two-step reaction was carried out. The first step is the formation of TMSI by mixing TMSCl with KI.…”

Section: Resultsmentioning

confidence: 99%

“…For Z-selective semi-reduction of the triyne 7 we used the modified Boland procedure. 12 The Zn(Cu/Ag) was prepared according to reported procedure in literature. 19 To a suspension of the Zn(Cu/Ag) (2.0 g) in MeOH:H2O (1:1, 6 mL), the triyne 7 (0.40 g, 0.08 mmol) was added and followed subsequently by the addition of trimethylsilyl chloride (TMSCl) (0.1 mL, 0.80 mmol).…”

Section: Methyl-9-(5-(hept-1-yn-1-yl)thiophen-2-yl)nona-58-diynoate (7)mentioning

confidence: 99%

“…The compound was isolated from the red alga Bossiella orbigniana by Burgess et al in 1991, 11 and the first total synthesis of methyl bosseopentaenoate 5b was published in 2011. 12 Herein, we report a synthetic strategy towards a thiophene analogue of BPA 6a as well as its biological activity evaluation in comparison with BPA 5a.…”

Section: Introductionmentioning

confidence: 99%

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An efficient stereoselective synthesis of a sulfur-bridged analogue of bosseopentaenoic acid as a potential antioxidant agent

Mohamed¹,

Solum²

2017

Arkivoc

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An efficient approach to the stereoselective synthesis of a novel sulfur-bridged analogue of bosseopentaenoic acid (BPA) by employing the Z-selective modified Boland semi-reduction procedure as the key step is described. The free radical scavenging potential of the thiophene analogue of bosseopentaenoic acid is studied. The results showed that the thiophene ring led to increased antioxidant activity.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methyl-9-(5-(hept-1-yn-1-yl)thiophen-2-yl)nona-58-diynoate (7)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

An efficient stereoselective synthesis of a sulfur-bridged analogue of bosseopentaenoic acid as a potential antioxidant agent

Mohamed¹,

Solum²

2017

Arkivoc

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“…For example, MIDA boronates have enabled the syntheses of (−)-aurantioclavine 22 via slow-release cross-coupling, 23 as well as elansolid B1, 24 (−)-myxalamide A, 25 eicosapentaenoate methyl ester, 26 marinoquinoline C and E, 27 and in other applications. 28 …”

Section: Accessing Linear Csp2-rich Small Molecules Via Iterativementioning

confidence: 99%

From Synthesis to Function via Iterative Assembly of N-Methyliminodiacetic Acid Boronate Building Blocks

2015

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Small molecules can powerfully benefit society, but the study and optimization of their function is too often impeded by the time-intensive and specialist-dependent process that is typically used to make them. In contrast, general and automated platforms have been developed for peptide, oligonucleotide, and increasingly oligosaccharide synthesis, resulting in on-demand access to these molecules, even for non-specialists. A more generalized and automated approach for making small molecules could similarly help shift the rate limiting step in small molecule science from synthesis to function. Targeting this goal, we have developed a fully automated and increasingly general platform for iterative coupling of boronate building blocks. Analogous to peptide synthesis, the process involves iterative coupling of haloboronic acids protected as the corresponding N-methyliminodiacetic acid (MIDA) boronates. This platform has enabled us and other groups to access many polyene natural products, including the polyene motifs in >75% of all polyene natural products. It further allowed us to derivatize and thereby understand the powerful but also highly toxic antifungal natural product amphotericin B, which has led to the development of less toxic derivatives currently under evaluation as drug candidates. We also discovered a stereocontrolled entry into chiral, non-racemic α-boryl aldehydes, which are versatile intermediates for the synthesis of many Csp3 boronate building blocks that are otherwise difficult to access. We have also expanded the scope of the platform to include Csp3-rich, polycyclic molecules using a linear-to-cyclized strategy, in which Csp3 boronate building blocks are iteratively assembled into linear precursors that are then cyclized into the cyclic frameworks found in many natural products and natural product-like structures. Enabled by the serendipitous discovery of a catch-and-release protocol for generally purifying MIDA boronate intermediates, the platform has been automated. The synthesis of 14 distinct classes of small molecules, including pharmaceuticals, materials, and polycyclic natural products has been achieved using this new synthesis machine. It is anticipated that the scope of small molecules accessible by this platform will continue to expand via further developments in building block synthesis, Csp3 cross-coupling methodologies, and cyclization strategies.

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Preparation of MIDA Anhydride and Reaction with Boronic Acids

et al. 2023

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This chapter describes the procedure for preparation of N ‐methyliminodiactic acid (MIDA) anhydride and reaction with boronic acids. It presents some of the important points to be considered, the conditions that need to be maintained, characterization data, and the reagents required, as well as the techniques used and the equipment setup that are vital to carrying out the process. The chapter also describes the hazards associated with working with chemicals and the ways to deal with these hazards. Boronic acids are amongst the most widely used reagents for the assembly of small organic molecules. The protection of boron with MIDA has broadly enabled the synthesis of many complex MIDA boronate building blocks using transformations otherwise incompatible with boronic acids. MIDA boronates possess an unusual binary affinity for silica gel.

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Synthesis of methyl (5Z,8Z,10E,12E,14Z)-eicosapentaenoate

Cited by 33 publications

References 26 publications

An efficient stereoselective synthesis of a sulfur-bridged analogue of bosseopentaenoic acid as a potential antioxidant agent

An efficient stereoselective synthesis of a sulfur-bridged analogue of bosseopentaenoic acid as a potential antioxidant agent

From Synthesis to Function via Iterative Assembly of N-Methyliminodiacetic Acid Boronate Building Blocks

Preparation of MIDA Anhydride and Reaction with Boronic Acids

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