The distinctively singular self-assembly of a “molecular stair”: observation of a quadrilateral C–H⋯O hydrogen bonding cycle in the crystal structure of a tetracyclic oligo-tetrahydrofuran

Rashid, Showkat; Bhat, Bilal A.; Sen, Saikat; Mehta, Goverdhan

doi:10.1039/c5ra13749g

Cited by 3 publications

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

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

et al. 2020

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Progress in the Total Synthesis of Natural Products Embodying Diverse Furofuranone Motifs: A New Millennium Update

2020

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Complex, functionally embellished natural products embodying diverse, oxygen rich furofuranone fragments like furo[3,4-c]furanone, furo[2,3-b]furanone, furo[3,4-b]furan-2(3H)-one, furo[3,4-b]furan-4(2H)-one and furo[3,4-b]furan-6(4H)-one as the key motif and displaying wide range of biological activities such as anti-cancer, anti-HIV, anti-microbial activities, etc., continue to draw considerable traction towards targeted synthesis, methodolgical developments as well as medicinal chemistry guided efforts. The challenging and tempting combination of complexity laden architecture and varied bioactivity profile, among the variegated furofuranone natural products has led to intense synthetic activity in the arena in recent years and culminated in the total synthesis of structurally diverse family of bioactive metabolites such as gracilioethers, syringolides, degraded spongianes etc. While comprehensively recounting the attainments in the total syntheses of furofuranone natural products in the past two decades (in the 21st century), this review attempts to identify the key tactics deployed in each synthetic campaign. This topical review aims at drawing and sustaining the interest of synthetic chemistry community in undertaking further creative pursuits towards this rich and enticing family of natural products while concurrently exploring the utility driven diversity space around them. Scheme 2. Pattenden's synthesis of (�)-anthecularin (ref. 11) Scheme 3. Watanabe's synthesis of (+)-anthecularin (ref. 12

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Advances in the synthesis of furo[2,3-b]furanone-containing natural products

Bhat

Rashid

Mehta

2019

Bioactive Natural Products

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The distinctively singular self-assembly of a “molecular stair”: observation of a quadrilateral C–H⋯O hydrogen bonding cycle in the crystal structure of a tetracyclic oligo-tetrahydrofuran

Abstract: A comparative analysis of the crystal structures of three structurally related molecular stairs has identified a rare C–H⋯O H-bonding motif and revealed the significant role played by the peripheral THF moieties in their modes of self-assembly.

Cited by 3 publications

References 15 publications

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

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

Progress in the Total Synthesis of Natural Products Embodying Diverse Furofuranone Motifs: A New Millennium Update

Advances in the synthesis of furo[2,3-b]furanone-containing natural products

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