Biosynthesis of alkyne-containing natural products

Li, Xinyang; Lv, Jian-Ming; Hu, Dan; Abe, Ikuro

doi:10.1039/d0cb00190b

Cited by 35 publications

(18 citation statements)

References 91 publications

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“…In particular, selective catalysis that leads to the formation of different products from the same starting material is a powerful tool for divergent synthesis. [277][278][279][280][281] Interestingly, employing oxone as an oxidant to carry out such crucial transformations without involving any acid or base, are of special interest as this versatile reagent is compatible with several functional groups. In this context, oxidative cyclization of the unprotected 2-alkynylanilines 330 to furnish the functionalized 4H-benzo[d] [1,3]oxazin-4-one 332 j or benzisoxazole derivatives 331 a-i by the selective catalysis of gold/silver with oxone was established by Arcadi et al, mentioned in the Scheme 110.…”

Section: Silver Vs Gold-catalyzed Oxidative Cyclizations Of 2-alkynyl...mentioning

confidence: 99%

“…Generally, the selectivity of the product formation is controlled by the modification of reaction conditions and have a significant challenge in the synthetic organic chemistry. In particular, selective catalysis that leads to the formation of different products from the same starting material is a powerful tool for divergent synthesis [277–281] . Interestingly, employing oxone as an oxidant to carry out such crucial transformations without involving any acid or base, are of special interest as this versatile reagent is compatible with several functional groups.…”

Section: Oxidation Of Diverse Functional Groupsmentioning

confidence: 99%

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Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

2022

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Presently, the major cornerstone of the research community is to develop green as well as sustainable protocols involving inexpensive catalysts and/or reagents without the usage of hazardous solvents under globally friendlier conditions in order to shelter both mankind and environment. Therefore, needless to say, there is always a supreme need to surrogate the older, costlier and unsafe strategies with the novel economically inexpensive and environmental benign ones. To this context, in recent past, oxone® (triple salt), a very cheap oxidizing agent having the chemical formula 2KHSO5 ⋅ KHSO4 ⋅ K2SO4 and enwrapped with the unique characteristics like easy handling, non‐toxic, safe, eco‐friendly, non‐polluting, stable, and nicely soluble in water, in addition to its utility for large‐scale synthesis etc. Bearing the importance of this versatile reagent in mind, we envisioned to update the recent advances made in this direction. Consequently, in this particular review article, the developments made in the arena of oxone chemistry covering from 2013 to 2020 have been revealed as no report appeared in the literature after a wonderful Chem. Rev. published by the group of Hussain in 2013. Herein, a comprehensive detail of a variety of oxidative transformations along with the complete plausible mechanistic steps have been exposed. For sure, present review would be a very helpful tool to the scientific community not only working in the area of organic synthesis but also to the researchers working in other branches of science and technologies as well.

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Section: Silver Vs Gold-catalyzed Oxidative Cyclizations Of 2-alkynyl...mentioning

confidence: 99%

Section: Oxidation Of Diverse Functional Groupsmentioning

confidence: 99%

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

2022

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“…So far, three monoacetylenic fatty acids (tariric acid, C 18:1Δ6 ; stearolic acid, C 18:1Δ9 ; and crepenynic acid, C 18:1Δ12 ) have been found, making it seem likely that there are at least three metabolic entry points into the structural space occupied by polyacetylenes. These have been dubbed the tarirate, stearoleate, and crepenynate pathways, respectively (Li et al., 2020; Minto & Blacklock, 2008; Negri, 2015).…”

Section: Main Textmentioning

confidence: 99%

Variation on a theme: the structures and biosynthesis of specialized fatty acid natural products in plants

2022

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SUMMARY Plants are able to construct lineage‐specific natural products from a wide array of their core metabolic pathways. Considerable progress has been made toward documenting and understanding, for example, phenylpropanoid natural products derived from phosphoenolpyruvate via the shikimate pathway, terpenoid compounds built using isopentyl pyrophosphate, and alkaloids generated by the extensive modification of amino acids. By comparison, natural products derived from fatty acids have received little attention, except for unusual fatty acids in seed oils and jasmonate‐like oxylipins. However, scattered but numerous reports show that plants are able to generate many structurally diverse compounds from fatty acids, including some with highly elaborate and unique structural features that have novel bioproduct functionalities. Furthermore, although recent work has shed light on multiple new fatty acid natural product biosynthesis pathways and products in diverse plant species, these discoveries have not been reviewed. The aims of this work, therefore, are to (i) review and systematize our current knowledge of the structures and biosynthesis of fatty acid‐derived natural products that are not seed oils or jasmonate‐type oxylipins, specifically, polyacetylenic, very‐long‐chain, and aromatic fatty acid‐derived natural products, and (ii) suggest priorities for future investigative steps that will bring our knowledge of fatty acid‐derived natural products closer to the levels of knowledge that we have attained for other phytochemical classes.

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“…The use of different alkynes results in a high structural variability of the enyne system. [5][6] The latter structural motif is of high interest because it is an elementary building block in many natural products [7][8][9][10] and can also be used for the construction of larger systems. [11][12] Accordingly, much effort has already been made in the field of hydroalkynylation and a wide range of internal alkynes have been used.…”

Section: Introductionmentioning

confidence: 99%

“…The use of different alkynes results in a high structural variability of the enyne system [5–6] . The latter structural motif is of high interest because it is an elementary building block in many natural products [7–10] and can also be used for the construction of larger systems [11–12] …”

Section: Introductionmentioning

confidence: 99%

Regio‐ and Stereoselective Synthesis of Ynenamides through Gold(I)‐Catalyzed Hydroalkynylation of Ynamides

et al. 2022

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Transition metal catalysis is a useful tool for C−C bond‐forming reactions. Of special interest is the hydroalkynylation reaction of alkynes, which provides a simple method for the synthesis of enynes representing interesting structural motifs in organic chemistry. So far, there are only a few examples of gold(I)‐catalyzed hydroalkynylation reactions. Herein, we were able to show experimentally that the gold(I)‐catalyzed hydroalkynylation of ynamides leads regio‐ and stereoselectively to the corresponding ynenamides, a rather unknown type of molecule. A wide range of products could be generated with yields up to 90 % and, in contrast to many other gold‐catalyzed alkyne dimerization reactions, alkyl groups are tolerated. Quantum chemical calculations and NMR labelling experiments reveal a mechanism via dual gold catalysis.

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Biosynthesis of alkyne-containing natural products

Abstract: This review comprehensive discusses the progress in the biosynthesis of alkyne-containing natural products and introduces de novo biosynthesis for in situ generating alkyne-tagged products.

Cited by 35 publications

References 91 publications

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

Variation on a theme: the structures and biosynthesis of specialized fatty acid natural products in plants

Regio‐ and Stereoselective Synthesis of Ynenamides through Gold(I)‐Catalyzed Hydroalkynylation of Ynamides

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