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

Bhat, Bilal A.; Rashid, Showkat; Sengupta, Saumitra; Mehta, Goverdhan

doi:10.1002/ajoc.201900714

Cited by 7 publications

(3 citation statements)

References 209 publications

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“…Compounds with such structural features have attracted attention not only for synthesis, 4 but also for testing biological activity, especially cytotoxicity. 5 Based on spectroscopic methods and ECD calculations, the structures of these new natural products, asperilactones B and C, were proposed.…”

Section: Introductionmentioning

confidence: 99%

First total synthesis of asperilactone B. Revision of absolute stereochemistry of asperilactones B and C

Djokić,

Benedeković,

Kesić

et al. 2024

Org. Biomol. Chem.

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Section: Introductionmentioning

confidence: 99%

First total synthesis of asperilactone B. Revision of absolute stereochemistry of asperilactones B and C

Djokić,

Benedeković,

Kesić

et al. 2024

Org. Biomol. Chem.

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“…In continuation of our deep interests in natural products total synthesis, [34][35][36][37][38][39] and their exploitation in medicinal chemistry, [40,41] platanic acid derived from betulinic acid was taken as a starting point for structural reformations. Based on the literature precedence, structural analoguing was executed on the side chain which is considered as one of the molecule's hot spots.…”

Section: Introductionmentioning

confidence: 99%

Platanic Acid‐Aryl Enones as Potential Anticancer Compounds: Synthesis and Biological Profiling against Breast, Prostate and Lung Cancer Cell Lines

Ganaie

Shahid

Rashid

et al. 2021

Chemistry & Biodiversity

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A series of rationally designed platanic acid‐based compounds derived from naturally occurring betulinic acid were synthesized through a sequence of Lemieux‐Johnson oxidation and Aldol condensation reaction. All the compounds were screened for cytotoxicity against a panel of human cancer and normal cell lines using MTT assay. From the biological data, it was observed that some of these semi‐synthetic congeners exhibited potent biological profiles compared to platanic acid. One of the compounds with the p‐tolyl substitution was found to be most active in this study, and its cytotoxicity against two of the cell lines, MDA‐MB 231 and A‐549 were in tune with the standard compound, 5‐fluorouracil.

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“…Based on the dispersal of oxygen atoms on the bicyclo[3.3.0]octane ring system, we have earlier categorized furofuranones into six sub‐types A – F (Figure 1). [6a] Among these sub‐types, synthetic advances towards furo[3,2‐ b ]furanone ( Type A ) and some examples of furo[2,3‐ b ]furanone ( Type C ) natural products have been covered in our recent contributions. [6a,b] Recognizing the growing interest of the synthetic organic chemistry community in the furofuranone sub‐types B – F (Figure 2) and significant advances witnessed during the last two decades, it is an appropriate time to document the total syntheses achievements in the arena, as a complementary sequel to our preceeding review [6a,b] …”

Section: Introductionmentioning

confidence: 99%

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

Cited by 7 publications

References 209 publications

First total synthesis of asperilactone B. Revision of absolute stereochemistry of asperilactones B and C

First total synthesis of asperilactone B. Revision of absolute stereochemistry of asperilactones B and C

Platanic Acid‐Aryl Enones as Potential Anticancer Compounds: Synthesis and Biological Profiling against Breast, Prostate and Lung Cancer Cell Lines

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

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