Denovo asymmetric synthesis of the mezzettiaside family of natural products via the iterative use of a dual B-/Pd-catalyzed glycosylation

Bajaj, Sumit O.; Sharif, Ehesan U.; Akhmedov, Novruz G.; O’Doherty, George A.

doi:10.1039/c4sc00593g

Cited by 80 publications

(57 citation statements)

References 37 publications

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“…1 H NMR and 13 C NMR spectra were taken on a JEOL JNM-ECP 600 spectrometer with tetramethylsilane as an internal standard, and chemical shifts were recorded in ppm values. 1 (14). 1-O-n-Octyl-2,3,4-tri-O-acetyl-α-L-rhamnopyranoside (9).…”

Section: Experimental Protocolsmentioning

confidence: 99%

Synthesis and biological evaluation of acylated oligorhamnoside derivatives structurally related to mezzettiaside-6 with cytotoxic activity

Song

Lei

et al. 2016

Org. Biomol. Chem.

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Two partially acylated oligorhamnoside derivatives 1 and 2 structurally related to the natural product mezzettiaside-6 were synthesized via a '2 + 1 + 1' convergent strategy. The bioassay results showed that the introduction of the acetyl groups to the 2-position of the terminal l-rhamnose was helpful to improve in vitro cytotoxicity. Compound 1 showed both extensive in vitro cytotoxicity in tumor cell lines and potential antimultidrug resistance capability. Preliminary mechanistic studies demonstrated that compound 1 could inhibit cell growth by inducing apoptosis, arresting cell cycle progression at the S phase in K562 cells.

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Section: Experimental Protocolsmentioning

confidence: 99%

Synthesis and biological evaluation of acylated oligorhamnoside derivatives structurally related to mezzettiaside-6 with cytotoxic activity

Song

Lei

et al. 2016

Org. Biomol. Chem.

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“…Recently,t he group of O'Doherty reported the de novo synthesis of complex mezzettiasides by boron/palladium cocatalyzed glycosylation (Scheme 26). [63] Monosaccharide A was prepared from the corresponding palladium-catalyzed glycosylation product followed by three steps of post-glycosylation modifications-reduction, dihydroxylation, and esterification. The palladium/boron cocatalyzed glycosylation of the diol in A was realizeds ite-selectivelyt oa fford the desired product B as the major isomer.T his strategy is very efficient when the equatorial OH is the desired glycosyl acceptor.S everald isaccharides were then prepareda fter functional transformations.…”

Section: Formation Of Dihydropyrans In Oligosaccharidesby Achmatowiczmentioning

confidence: 99%

De Novo Synthesis of Mono‐ and Oligosaccharides via Dihydropyran Intermediates

Song

Wang

Tang

2017

Chemistry An Asian Journal

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The importance of carbohydrates is evident by their essential role in all living systems. Their syntheses have attracted attention from chemists for over a century. Most chemical syntheses in this area focus on the preparation of carbohydrates from naturally occurring monosaccharides. De novo chemical synthesis of carbohydrates from feedstock starting materials has emerged as a complementary method for the preparation of diverse mono- and oligosaccharides. In this review, the history of de novo carbohydrate synthesis is briefly discussed and particular attention is given to methods that address the formation of glycosidic bonds for potential de novo synthesis of oligosaccharides. Almost all methods of this kind involve the formation of dihydropyran intermediates. Recent progress in forming dihydropyrans by Achmatowicz rearrangement, hetero-Diels-Alder cycloaddition, ring-closing metathesis, and other methods is also elaborated.

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“…302 Mezzettiaside-2 ( 271 ) and congeners were synthesized as anticancer/antibiotic oligosaccharides. 88 Merremoside D 272 299 and carbohydrates including digitoxin ( 273 , anticancer properties), 303 vineomycinone B2 ( 274 ), 304 vineomycin B2 trisaccharide ( 276 ) 305 (antitumor and antibacterial activities), methymycin analogues such as 275 (antibiotic activity), 306 and landomycins A and E ( 277a,b , antitumor activity) 307 were also synthesized using these protocols.…”

Section: Introductionmentioning

confidence: 99%

Achmatowicz reaction and its application in the syntheses of bioactive molecules

Ghosh

Brindisi

2016

RSC Adv.

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Substituted pyranones and tetrahydropyrans are structural subunits of many bioactive natural products. Considerable efforts are devoted toward the chemical synthesis of these natural products due to their therapeutic potential as well as low natural abundance. These embedded pyranones and tetrahydropyran structural motifs have been the subject of synthetic interest over the years. While there are methods available for the syntheses of these subunits, there are issues related to regio and stereochemical outcomes, as well as versatility and compatibility of reaction conditions and functional group tolerance. The Achmatowicz reaction, an oxidative ring enlargement of furyl alcohol, was developed in the 1970s. The reaction provides a unique entry to a variety of pyranone derivatives from functionalized furanyl alcohols. These pyranones provide convenient access to substituted tetrahydropyran derivatives. This review outlines general approaches to the synthesis of tetrahydropyrans, covering general mechanistic aspects of the Achmatowicz reaction or rearrangement with an overview of the reagents utilized for the Achmatowicz reaction. The review then focuses on the synthesis of functionalized tetrahydropyrans and pyranones and their applications in the synthesis of natural products and medicinal agents.

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Denovo asymmetric synthesis of the mezzettiaside family of natural products via the iterative use of a dual B-/Pd-catalyzed glycosylation

Cited by 80 publications

References 37 publications

Synthesis and biological evaluation of acylated oligorhamnoside derivatives structurally related to mezzettiaside-6 with cytotoxic activity

Synthesis and biological evaluation of acylated oligorhamnoside derivatives structurally related to mezzettiaside-6 with cytotoxic activity

De Novo Synthesis of Mono‐ and Oligosaccharides via Dihydropyran Intermediates

Achmatowicz reaction and its application in the syntheses of bioactive molecules

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