Synthesis of 3,5-dideoxy-5-iodo-1,2-O-isopropylidene-β-l-lyxo-hexofuranose derivatives

Rondot, B.; Rossi, Jean‐Claude; Rollin, Patrick

doi:10.1016/0008-6215(94)80013-8

Cited by 15 publications

(9 citation statements)

References 18 publications

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“…At the beginning of the 1990s, the Durand/ Rossi group along with Rokach's team reported the synthesis of key intermediate 6, a diastereomer of Corey's formyl-lactone, via an acyclic thionocarbonate [36]. Durand and Rossi developed subsequently radical carbocyclizations of functionalized iodo precursors 8 and 9 (Scheme 2) [37], which replace the thionocarbonate precursors initially proposed advantageously. The synthesis of 6 started with commercially available 1,2,5,6-di-O-isopropylidene-a-D-glucofuranose D-10, which was transformed to the corresponding 3-deoxy-sugar 11 in 85% yield using the Barton-McCombie procedure.…”

Section: Cyclization Reactions Followed By Attachment Of the Remaininmentioning

confidence: 98%

“…Introduction of iodine at C5 to 14 was accomplished in 96% yield by using I 2 , Ph 3 P and imidazole in xylene in a procedure developed earlier by our group [37]. Hydrolysis of the isopropylidene group at 1,2-position was achieved in the presence of 10% aqueous sulfuric acid in THF-dioxane (3:1) to afford the diol 15 in 86% yield.…”

Section: Cyclization Reactions Followed By Attachment Of the Remaininmentioning

confidence: 99%

“…Radical Cyclizations Since radical cyclizations are wellsuited to approach cyclopentane rings with cis-oriented substituents [35] DMF and imidazole led to the pure mono silyl ether 13. Introduction of iodine at C5 to 14 was accomplished in 96% yield by using I 2 , Ph 3 P and imidazole in xylene in a procedure developed earlier by our group [37]. Hydrolysis of the isopropylidene group at 1,2-position was achieved in the presence of 10% aqueous sulfuric acid in THF-dioxane (3:1) to afford the diol 15 in 86% yield.…”

Section: Cyclization Reactions Followed By Attachment Of the Remaininmentioning

confidence: 99%

“…Conversion of the primary alcohol 22 into the methyl ester 33 was achieved using a three-step protocol. Alcohol (12E)-32 was oxidized with Dess-Martin periodinane and subsequently sodium chlorite to the Scheme 2 Synthesis of cyclopentane key intermediates according to Durand, Rossi and co-workers [37] corresponding carboxylic acid, which was esterified with (trimethylsilyl)diazomethane in good yield. The total synthesis was completed by retro-Diels-Alder reaction of the cyclopentadienyl-protected methyl ester 33 with MeAlCl 2 and maleic anhydride under microwave conditions to give 52% of (±)-trans-D 12,14 -15-deoxy-PGJ 1 methyl ester 34 and 14% of its cis-isomer (not shown).…”

Section: Cyclization Reactions Followed By Attachment Of the Remaininmentioning

confidence: 99%

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New Bioactive Oxylipins Formed by Non‐Enzymatic Free‐Radical‐Catalyzed Pathways: the Phytoprostanes

Durand

Bultel-Poncé

Guy

et al. 2009

Lipids

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In animals and plants, fatty acids with at least three double bonds can be oxidized to prostaglandin-like compounds via enzymatic and non-enzymatic pathways. The most common fatty acid precursor in mammals is arachidonic acid (C20:4) (AA) which can be converted through the cyclooxygenase pathway to a series of prostaglandins (PG). Non-enzymatic cyclization of arachidonate yields a series of isoprostanes (IsoP) which comprises all PG (minor compounds) as well as PG isomers that cannot be formed enzymatically. In contrast, in plants, alpha-linolenic acid (C18:3) (ALA) is the most common substrate for the allene oxide synthase pathway leading to the jasmonate (JA) family of lipid mediators. Non-enzymatic oxidation of linolenate leads to a series of C18-IsoPs termed dinor IsoP or phytoprostanes (PP). PP structurally resemble JA but cannot be formed enzymatically. We will give an overview of the biological activity of the different classes of PP and also discuss their analytical applications and the strategies developed so far for the total synthesis of PP, depending on the synthetic approaches according to the targets and which key steps serve to access the natural products.

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Section: Cyclization Reactions Followed By Attachment Of the Remaininmentioning

confidence: 98%

Section: Cyclization Reactions Followed By Attachment Of the Remaininmentioning

confidence: 99%

Section: Cyclization Reactions Followed By Attachment Of the Remaininmentioning

confidence: 99%

Section: Cyclization Reactions Followed By Attachment Of the Remaininmentioning

confidence: 99%

See 2 more Smart Citations

New Bioactive Oxylipins Formed by Non‐Enzymatic Free‐Radical‐Catalyzed Pathways: the Phytoprostanes

Durand

Bultel-Poncé

Guy

et al. 2009

Lipids

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“…Introduction of iodine at C5 to give 221 was accomplished in 96 % yield by using I 2 , Ph 3 P, and imidazole in xylene in a procedure developed earlier by Durand, Rossi, and co-workers. [239] Hydrolysis of the isopropylidene group at the 1,2-position was achieved in the presence of 10 % aqueous sulfuric acid in THF/dioxane (3:1) to afford the diol 222 in 86 % yield. The next step was a Wittig reaction with methyl triphenylphosphoranylideneacetate, which afforded the cyclization precursor 223 in 75 % yield.…”

Section: From Cyclopentane Precursors Bearing Additional Carbon Atomsmentioning

confidence: 99%

Beyond Prostaglandins—Chemistry and Biology of Cyclic Oxygenated Metabolites Formed by Free‐Radical Pathways from Polyunsaturated Fatty Acids

2008

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Polyunsaturated fatty acids (PUFAs) are important constituents in all organisms. They fulfil many functions, ranging from modulating the structure of membranes to acting as precursors of physiologically important molecules, such as the prostaglandins, which for a long time were the most prominent cyclic PUFA metabolites. However, since the beginning of the 1990s a large variety of cyclic metabolites have been discovered that form under autoxidative conditions in vivo to a much larger extent than do prostaglandins. These compounds--isoprostanes, neuroprostanes, phytoprostanes, and isofurans--proved subsequently to be ubiquitous in nature. They display a wide range of biological activities, and isoprostanes have become the currently most reliable indicators of oxidative stress in humans. In a relatively short time, the structural variety, properties, and applications of the autoxidatively formed cyclic PUFA derivatives have been uncovered.

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Total Synthesis of Marine Natural Products: Cephalosporolides

Halle

Fernandes

2016

Asian J Org Chem

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Marine-derived species, in particular, fungi, algae, sponges, and coelenterates are fertile grounds for the discovery of biologically and pharmacologically potent compounds. These molecules are structurally unique and possess a wide range of pharmacological activities. The rigid spiroacetal framework, that is, tetrahydro-spirofurofuranones is present in cephalosporolides E, F, H, and I, while the macrolactone structure is exemplified by cephalosporolides B, C, D, G, and J. These marine-derived molecular architectures are appealing to the synthetic community for their stereoselective synthesis. The present review represents a comprehensive overview of all the reported syntheses of these marine-derived molecules.

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Synthesis of 3,5-dideoxy-5-iodo-1,2-O-isopropylidene-β-l-lyxo-hexofuranose derivatives

Cited by 15 publications

References 18 publications

New Bioactive Oxylipins Formed by Non‐Enzymatic Free‐Radical‐Catalyzed Pathways: the Phytoprostanes

New Bioactive Oxylipins Formed by Non‐Enzymatic Free‐Radical‐Catalyzed Pathways: the Phytoprostanes

Beyond Prostaglandins—Chemistry and Biology of Cyclic Oxygenated Metabolites Formed by Free‐Radical Pathways from Polyunsaturated Fatty Acids

Total Synthesis of Marine Natural Products: Cephalosporolides

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