Regioselective Synthesis of Novel 7-5-8-Fused Oxabridged Tricyclic Molecules via Consecutive Dipolar Cycloaddition of Pentafulvenes with 3-Oxidopyrylium Betaines

Krishnan, Karthik; Suresh, Eringathodi; Mathew, Saumini; Radhakrishnan, K. V.

doi:10.1055/s-2006-942366

Cited by 4 publications

(2 citation statements)

References 2 publications

(4 reference statements)

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“…These modifications led to oxa-bridged cyclooctanoids having an outstanding synthetic value, as these can act as key intermediates in the synthesis of various biologically relevant molecular frameworks (Scheme ). − …”

Section: Cycloaddition Chemistry Of Pentafulvenesmentioning

confidence: 99%

Recent Advances in the Chemistry of Pentafulvenes

et al. 2017

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Pentafulvenes are a unique class of compounds that originally attracted attention due to their propensity to display nonbenzenoid aromaticity. Subsequently, they were recognized as valuable synthons for the construction of a wide range of compounds by virtue of their ability to display multiple cycloaddition profiles. Naturally, this area of organic chemistry has experienced rapid growth over the last five decades, fueled by elegant work showcasing the unique reactivity of pentafulvenes in a plethora of cycloaddition reactions. In this Review, we have attempted to provide a systematic account of the methods for the generation of pentafulvenes, their rich and varied cycloaddition chemistry, organometallic reactions, and theoretical studies that support their versatility. Further, we have highlighted their applications in the synthesis of a variety of complex structural frameworks. It is our conviction that this Review will be useful to a wide range of chemists, and will spur further research in this promising area.

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Section: Cycloaddition Chemistry Of Pentafulvenesmentioning

confidence: 99%

Recent Advances in the Chemistry of Pentafulvenes

et al. 2017

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“…Fulvenes are a class of cross-conjugated, cyclic molecules that exhibit unique reactivity resulting from their exocyclic double bond. , Pentafulvenes are capable of participating in various cycloadditions as 2π, 4π, and 6π components depending on the nature of the other reactant partner and fulvene substituents, and in many cases the reactions are peri-, enantio-, diastereo-, and regioselective. − Thus, pentafulvenes have been extensively employed in the synthesis of complex natural product polycyclic scaffolds. − In particular, 6,6-dialkyl pentafulvenes can be easily accessed in comparison to other bioconjugation agents, often producing high yields (>90%) in a single-step reaction from ketones without the use of expensive reagents or specialized equipment . Furthermore, the synthetic conditions are tolerant of various protic and nucleophilic functional groups ( e.g ., carboxylic acids and alcohols), allowing direct access to functional dialkyl pentafulvenes without the requirement for protecting group chemistries .…”

Section: Introductionmentioning

confidence: 99%

Pentafulvene–Maleimide Cycloaddition for Bioorthogonal Ligation

Platts

Robert²,

Green³

et al. 2021

Bioconjugate Chem.

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The applications of bioconjugation chemistry are rapidly expanding, and the addition of new strategies to the bioconjugation and ligation toolbox will further advance progress in this field. Herein, we present a detailed study of the Diels–Alder cycloaddition (DAC) reaction between pentafulvenes and maleimides in aqueous solutions and investigate the reaction as an emerging bioconjugation strategy. The DAC reactions were found to proceed efficiently, quantitatively yielding cycloadducts with reaction rates ranging up to ∼0.7 M–1 s–1 for a series of maleimides, including maleimide-derivatized peptides and proteins. The absence of cross-reactivity of the pentafulvene with a large panel of functional (bio)molecules and biological media further demonstrated the bioorthogonality of this approach. The utility of the DAC reaction for bioorthogonal bioconjugation applications was further demonstrated in the presence of biological media and proteins, as well as through protein derivatization and labeling, which was comparable to the widely employed sulfhydryl–maleimide coupling chemistry.

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Heterocycles via Pyrylium and Pyridinium Betaines

Radhakrishnan

Topics in Heterocyclic Chemistry

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Regioselective Synthesis of Novel 7-5-8-Fused Oxabridged Tricyclic Molecules via Consecutive Dipolar Cycloaddition of Pentafulvenes with 3-Oxidopyrylium Betaines

Abstract: Pentafulvenes undergo consecutive dipolar cycloadditions with various substituted oxidopyrylium betaines resulting in the formation of a new class of structurally interesting 7-5-8-fused oxabridged tricyclic molecules.

Cited by 4 publications

References 2 publications

Recent Advances in the Chemistry of Pentafulvenes

Recent Advances in the Chemistry of Pentafulvenes

Pentafulvene–Maleimide Cycloaddition for Bioorthogonal Ligation

Heterocycles via Pyrylium and Pyridinium Betaines

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