Studies Toward the Total Synthesis of Pluraflavin A

Hartung, J. B.; Wright, Benjamin J. D.; Danishefsky, Samuel J.

doi:10.1002/chem.201402254

Cited by 24 publications

(15 citation statements)

References 75 publications

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“…This was achieved by activating the epi -vancosamine trichloroacetimidate 145 with BF 3 ·OEt 2 in the presence of the protected pluraflavin A aglycone 146 at −40 °C to afford the glycoside 147 in 48% yield as a single β-isomer ( Scheme 43 ). 179 …”

Section: Direct Synthesismentioning

confidence: 99%

Methods for 2-Deoxyglycoside Synthesis

2018

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Deoxy-sugars often play a critical role in modulating the potency of many bioactive natural products. Accordingly, there has been sustained interest in methods for their synthesis over the past several decades. The focus of much of this work has been on developing new glycosylation reactions that permit the mild and selective construction of deoxyglycosides. This Review covers classical approaches to deoxyglycoside synthesis, as well as more recently developed chemistry that aims to control the selectivity of the reaction through rational design of the promoter. Where relevant, the application of this chemistry to natural product synthesis will also be described.

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Section: Direct Synthesismentioning

confidence: 99%

Methods for 2-Deoxyglycoside Synthesis

2018

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“…In this case, the choice of solvent played a crucial role in the ratio between α‐ and β‐selectivity . Due to the high toxicity of the stannyl compounds required for the Stille‐coupling, the 4,5‐disubstituted phthalonitrile 34 and the 3,6‐regioisomer 39 were synthesized through a Suzuki–Miyaura coupling in yields of 64–85 % here instead (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…Unfortunately, reduction of the double bonds in 34 did not work. The starting material was reisolated under various conditions tested so far (hydrogenation with Pd/C in hexane, ethyl acetate, toluene, methanol and ethyl acetate, with Pt/C in ethanol and with Pd(OH) 2 in ethanol , BH 3 · SMe 2 ,, and 9‐BBN were also tested for hydroboration of the double bonds but did not react with 34 either.…”

Section: Resultsmentioning

confidence: 99%

Glycoconjugated Phthalocyanines as Photosensitizers for PDT – Overcoming Aggregation in Solution

2019

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A series of new glycoconjugated zinc(II) phthalocyanines (Pcs) was synthesized and fully characterized. The major focus of the structural design for these new Pcs was upon the reduction of aggregate formation in solution. Therefore, the aglycons of the Pc‐linked sugars, the number and the position of the carbohydrate substituents on the Pc and the linker between sugar and Pc were varied. Specifically, di‐ and octasubstituted zinc(II) phthalocyanines with triazole and C–C linkages were synthesized and their aggregation behaviour was investigated by UV/Vis‐, CD‐ and NMR spectroscopy. The C‐glycosidically decorated Pcs described here are the first compound types of this kind. These C‐glycosidically substituted Pcs were shown to not form any aggregation in solution and hence, are considered to be potential photosensitizers in photodynamic therapy. All Pcs synthesized in this study exhibited excellent photophysical properties for use as photosensitizers (λmax > 675 nm with εmax > 105 m–1 cm–1). Preliminary cytotoxicity studies of the Pcs presented here showed that all Pcs are photodynamically effective.

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“…δ-lactones and stereoselective reduction of the resultant hemiacetals (route C), 28 and C(sp 2 )-C(sp 2 ) cross-coupling followed by reduction (route D). 29 All of the above methods suffer from a limited substrate scope (hydroxyl groups substituted as Ac, Bz, or Piv esters) and poor anomeric control if no participating groups are available to direct the formation of the 1,2-trans diastereomers. 25 Only in the presence of a directing group at C2, can high selectivity of the newly formed glycosidic C-C bond be achieved.…”

Section: Synpacts Syn Lettmentioning

confidence: 99%

Glycosyl Stille Cross-Coupling with Anomeric Nucleophiles – A General Solution to a Long-Standing Problem of Stereocontrolled Synthesis of C-Glycosides

Zhu

Yang

Walczak

2017

Synlett

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Aryl C-glycosides are common structural motifs found in bioactive natural products and commercially available drugs. Despite their importance, most chemical methods to prepare C-glycosides have relied on the nucleophilic addition/substitution of a glycosyl electrophile, which result in variable anomeric selectivities and yields. Furthermore, these methods are not compatible with saccharides containing free hydroxyl groups. Here, we describe a direct cross-coupling reaction of anomeric nucleophiles (anomeric stannanes) and aryl halides. This method is the first general approach to the synthesis of aryl C-glycosides resulting in exclusive anomeric selectivities for both anomers for a broad range of aryl and carbohydrate coupling partners (including unprotected saccharides).1 Introduction2 Synthesis of Anomeric Stannanes3 Glycosyl Stille Cross-Coupling4 Future Outlook5 Summary

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Studies Toward the Total Synthesis of Pluraflavin A

Cited by 24 publications

References 75 publications

Methods for 2-Deoxyglycoside Synthesis

Methods for 2-Deoxyglycoside Synthesis

Glycoconjugated Phthalocyanines as Photosensitizers for PDT – Overcoming Aggregation in Solution

Glycosyl Stille Cross-Coupling with Anomeric Nucleophiles – A General Solution to a Long-Standing Problem of Stereocontrolled Synthesis of C-Glycosides

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