Study of Stereoselectivity in Organometallic Additions to 1,2-O-Isopropylidene-O-R-α-D-xylopentodialdo-1,4-furanose

Gracza, Tibor; Szolcsányi, Peter

doi:10.3390/51201386

Cited by 16 publications

(10 citation statements)

References 21 publications

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“…First, 3‐ O ‐ tert ‐butyldimethylsilyl‐1,2:5,6‐di‐ O ‐isopropylidene‐α‐ D ‐glucofuranose ( 2 )11 was prepared from commercially available 1,2:5,6‐di‐ O ‐isopropylidene‐α‐ D ‐glucofuranose ( 1 ). Selective hydrolysis of 2 by using aqueous 70 % acetic acid at room temperature gave 5,6‐diol 3 11 in 85 % yield, which underwent oxidative degradation in the presence of sodium metaperiodate in aqueous methanol to afford the corresponding unstable aldehyde 4 ( F , Scheme ) 11a…”

Section: Methodsmentioning

confidence: 99%

A Concise Total Synthesis of (+)‐Pancratistatin from D‐Glucose Featuring the Henry Reaction

et al. 2013

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Pancratistatin (PST, Scheme 1) is a natural compound that was first isolated [1] from Spider Lily, a plant native to Hawaii that belongs to the Amaryllidaceae family. As well as antiviral and antiparasitic activities, PST has very strong antitumor activity. [2] Furthermore, PST can act as an antitumor secondary metabolite that can induce apoptosis in tumor cells by targeting their mitochondria while leaving normal cells unaffected. [3] Therefore, as well as being a challenging compound to synthetic chemists, a facile large-scale synthesis of PST and its analogs would be of great importance in pharmaceutical sciences. [4,5] However, despite many attempts to synthesize PST and its analogs (various epimers and/or deoxy derivatives, Scheme 1), [4g,h,j] a practical and scalable synthesis of from readily available starting compounds has remained elusive.We have been engaged in the total syntheses of naturally occurring branched-chain cyclitol compounds, such as cyclophellitol, mytillitol, laminitol, and (À)-tetrodotoxin (TTX), [6] by using d-glucose as the starting material. Herein, we describe the concise stereoselective total synthesis of (+)-PST from d-glucose, which features both inter-and intramolecular Henry reactions [7] (nitroaldol reactions) as key transformations. As shown in the retrosynthetic plan (Scheme 2), the key intermediate C-aryl nitrocyclitol B can be prepared from D by the intramolecular [a] Assoc. Scheme 1. Pancratistatin (PST) and its related compounds. Scheme 2. Retrosynthetic analysis of (+)-PST from d-glucose featuring an intramolecular Henry reaction.

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Section: Methodsmentioning

confidence: 99%

A Concise Total Synthesis of (+)‐Pancratistatin from D‐Glucose Featuring the Henry Reaction

et al. 2013

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“…A concise synthesis of (+) ‐25 involving a highly stereoselective nucleophilic substitution at the anomeric position of 1,2‐ O ‐isopropylidene furanose derivative 66 , readily obtainable from diacetone‐D‐allofuranose 65 , has been reported by Sartillo‐Piscil's group (Scheme ) . Lewis acid‐mediated stereoselective opening of the acetonide moiety in 66 with allyltrimethylsilane and sequential dihydroxylation and oxidative cleavage followed by PCC oxidation led to the bicylic lactone 68 .…”

Section: Total Synthesis Of Furo[32‐b]furanone Natural Productsmentioning

confidence: 99%

“…[12] They are postulated to arise via the shikimic acid pathway. (+)-Crassalactone B (26) and C (27) are naturally occurring cinnamoyl derivatives of (+)-1 that were isolated from the leaves and twigs of Polyalthia crassa and found to be mildly cytotoxic. [13] Owing to their interesting construct and potential biological activity, a large number of syntheses of these natural products have appeared in literature prior to 2000.…”

Section: Styryl Lactonesmentioning

confidence: 99%

“…Intermediate 47 was also converted to (+)-7-epi-goniofufurone (25) via Carylglycoside 50. The authors also utilized the intermediate 47 for the synthesis of (+)-crassalactone C (27) in three steps. Starting from D-glucose, Popsavin's group also synthesized (+)-crassalactone B (26).…”

Section: Popsavin Synthesis Of (+)-Goniofufurone (1) (+)-7-epi-goniomentioning

confidence: 99%

“…Deprotection of the allyl and Bn groups in 73 then produced (+)-goniofufurone (1) (Scheme 8). [29] Intermediates 70 and 71 were also elaborated to (+)-crassalactone C (27) and B (26), respectively via known chemistry (Scheme 8). [29]…”

Section: Mallesham Synthesis Of (+)-Goniofufurone (1) (+)-Crassalactmentioning

confidence: 99%

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Recent Advances in Total Synthesis of Bioactive Furo[3,2‐b]furanone Natural Products

et al. 2020

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The ubiquitous presence of highly oxygenated furo[3,2‐b]furanone fragments in diverse natural products with wide range of biological activities such as anti‐cancer, anti‐HIV, anti‐microbial activities, etc., has augmented their appeal both for synthetic and medicinal chemistry campaigns. Enticed by their potent biological activities and challenging polycyclic architecture, total synthesis of furo[3,2‐b]furanone natural products has witnessed intense activity in recent years with many notable achievements in the synthesis of structurally embellished family of bioactive metabolites such as plakortones, lactonamycines, schisanartanes, etc. While presenting a comprehensive account of post‐2000 syntheses of these natural products, through strategic and nuanced use of modern tools of organic synthesis, this review also aims to stimulate interest in exploring the diversity space around these natural products for newer applications.

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Synthese von Inhaltsstoffen der Amaryllisgewächse und nichtnatürlichen Derivaten

et al. 2016

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Dieser Aufsatz behandelt die Fortschritte bei der Synthese von Amaryllidaceae‐Alkaloiden seit der Veröffentlichung des letzten umfassenden Übersichtsartikels im Jahr 2008. Synthesen der Hauptinhaltsstoffe – Pancratistatin, 7‐Desoxypancratistatin, Narciclasin, Lycoricidin und Lycorin – sowie anderer natürlicher Inhaltsstoffe und nichtnatürlicher Derivate werden vorgestellt, und die biologische Aktivität der nichtnatürlichen Derivate wird diskutiert. Ein Ausblick und weitere Entwicklungen auf dem Gebiet beschließen den Aufsatz. Die Literatur wurde bis Ende August 2015 berücksichtigt.

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Study of Stereoselectivity in Organometallic Additions to 1,2-O-Isopropylidene-O-R-α-D-xylopentodialdo-1,4-furanose

Abstract: Diastereofacial selectivity of the addition of organometallic reagents to 1,2-Oisopropylidene-O-R-α-D-xylopentodialdo-1,4-furanoses (6) was studied.

Cited by 16 publications

References 21 publications

A Concise Total Synthesis of (+)‐Pancratistatin from D‐Glucose Featuring the Henry Reaction

A Concise Total Synthesis of (+)‐Pancratistatin from D‐Glucose Featuring the Henry Reaction

Recent Advances in Total Synthesis of Bioactive Furo[3,2‐b]furanone Natural Products

Synthese von Inhaltsstoffen der Amaryllisgewächse und nichtnatürlichen Derivaten

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