Stereoselective synthesis of methyl β-dl-novioside

Achmatowicz, O.; Grynkiewicz, Grzegorz; Szechner, Barbara

doi:10.1016/s0040-4020(01)83234-8

Cited by 46 publications

(14 citation statements)

References 15 publications

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“…It was first synthesized by Kiss et al [4] in 1964 starting from 1,2 : 5,6-di-O-isopropylidene-a-d-glucofuranose, which was transformed into a 1,1-dimethyl-d-glucitol derivative, then oxidized to epi-noviose and isomerized to ()-22 in 15 steps. In 1976, Achmatowicz Jr. et al [5] published a total synthesis in the racemic series starting from 2-acetylfuran, which, after Grignard reaction, acetylation, and hydrolysis yielded the keto-sugar derivative; reduction, methylation, and cis-hydroxylation led to the methyl glycoside of 22. The most recent approach to noviose was reported by Klemer et al [6] in 1986, involving a route of seven steps starting from l-rhamnose, which was oxidized after protection, then subjected to a Grignard reaction, and transformed to pyranose by deprotection; after renewed protection, methylation, and hydrolysis, ()-l-noviose (()-22) was obtained.…”

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confidence: 99%

Enantiospecific Total Synthesis of (−)-D-Noviose

Pankau

Kreiser

1998

HCA

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confidence: 99%

Enantiospecific Total Synthesis of (−)-D-Noviose

Pankau

Kreiser

1998

HCA

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“…10 The obtained pyranones were subsequently used in the preparation of various glycosidic buiding blocks, 11 such as the antibiotic sugar β-novioside, as an illustration of their synthetic potential. 12 Scheme 4 Achmatowicz's two-step approach towards 6-hydroxypyranones Achmatowicz's protocol was readily taken up by other groups and used in more complex synthetic projects. One advantage of the oxidative furan rearrangement proved to be the fact that the stereochemical information of the exocyclic hydroxyl carbon of the furylcarbinols could be smoothly transferred to the C-2 center of the O-heterocyclic products without loss of optical purity.…”

Section: Syn Thesismentioning

confidence: 99%

The Achmatowicz Rearrangement – Oxidative Ring Expansion of Furfuryl Alcohols

2015

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Over the years, the oxidative ring enlargement of furfuryl alcohols, known as the Achmatowicz reaction, has been developed into a powerful and versatile synthetic tool for the preparation of 6-hydroxypyranones. This review provides a comprehensive collection of the various ways to perform Achmatowicz rearrangement reactions and explores the role of this ring-expansion process in contemporary organic synthesis. 1 Introduction 2 Classical Methods and Variants 3 Single-Electron-Transfer Oxidations 4 Metal-Catalyzed Ring Expansions 5 Photolytic Oxygenations 6 Enzymatic Transformations 7 Conclusions

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“…Achmatowicz and co-workers converted furans to dihydropyranones by similar oxidative and hydrolytic conditions (Figure 3). 62, 63 The Achmatowicz reaction essentially represents an oxidative cleavage of a furan ring followed by an intramolecular cyclization, providing 6-hydroxy-2 H -pyran-2(3 H )-ones in mild conditions (Figure 1). 64 Oxidative ring expansion of furfuryl amines is known as the aza-Achmatowicz reaction (Figure 1), and provides substituted dihydropyridinones.…”

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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Stereoselective synthesis of methyl β-dl-novioside

Cited by 46 publications

References 15 publications

Enantiospecific Total Synthesis of (−)-D-Noviose

Enantiospecific Total Synthesis of (−)-D-Noviose

The Achmatowicz Rearrangement – Oxidative Ring Expansion of Furfuryl Alcohols

Achmatowicz reaction and its application in the syntheses of bioactive molecules

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