Scaffold Diversity Synthesis with Branching Cascades Strategy

Kumar, Kamal

doi:10.1002/9783527687503.ch27

Cited by 7 publications

(3 citation statements)

References 66 publications

(80 reference statements)

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“…Through the present work, we elucidate the development of a new substrate-based diversity-oriented folding strategy leading to the synthesis of cyclopropa-fused tetralones ( 3 ) and indeno-spirocyclopropanes ( 5 and 7 ), originating out of the reaction between DOSM and the enone-tethered substrates 2 , 4 , and 6 , respectively (Scheme ). The cyclopropanoids were subsequently elaborated in one step to privileged scaffolds such as tetralones, indenones, and fluorenones.…”

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confidence: 99%

Synthesis of Cyclopropanoids via Substrate-Based Cyclization Pathways

2018

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A series of unexpected reactions triggered by the dimethyloxosulfonium methylide led to the discovery of unconventional approaches for the synthesis of cyclopropafused tetralones and indeno-spirocyclopropanes. These highly functionalized structures were further elaborated in one step to privileged scaffolds such as tetralones, indenones, and fluorenones. As a whole, the results presented herein establish new diversity-oriented folding pathways.

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confidence: 99%

Synthesis of Cyclopropanoids via Substrate-Based Cyclization Pathways

2018

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“…The pursuit of synthetic methodologies that enable the rapid, straightforward construction of polycyclic frameworks from relatively simple, easily available starting materials through the formation of two or more covalent bonds in a single operation has been a common practice in organic synthesis . In this context, one-pot double intramolecular cyclization reactions have proven to be extremely powerful protocols.…”

Section: Introductionmentioning

confidence: 99%

One-Pot Double Intramolecular Cyclization Approach to Tetralin-Based Cis-Fused Tetracyclic Compounds

Das

2022

J. Org. Chem.

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Presented herein is a BF 3 •OEt 2 -mediated, diastereoselective one-pot double cyclization of 4-aryl-2-[(arylthio)methyl]butanals leading to the formation of cis-tetrahydro-6H-naphtho[2,1-c]thiochromenes for the first time. Mechanistically, the formation of the title products involves the one-pot intramolecular Friedel−Crafts hydroxyalkylation/intramolecular Friedel−Crafts alkylation cascade. This synthetic methodology is featured by its high atom economy, broad substrate scope, mild transition-metalfree reaction conditions, capability to assemble two new rings in one pot, and moderate to high yields (up to 94% yield). It was then applied in the synthesis of a thia analogue of brazilane and a chromeno[3,4-c]chromene derivative. Moreover, the methodology was successfully extended to the synthesis of cis-hexahydrobenzo[c]phenanthrenes. Specifically, 1,5-diarylpentan-3-ones were first subjected to the Corey−Chaykovsky reaction, and the resulting epoxides, without being chromatographically isolated, were treated with BF 3 •OEt 2 to afford the cyclized products in high yields (up to 84% yield over two steps).

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“…Step and atom economical regioselective and stereoselective construction of highly functionalized complex molecules from simple building blocks has significant importance in modern synthetic organic chemistry . The scalable synthesis of such scaffolds with structural diversity for biological studies in drug discovery is still challenging to date.…”

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confidence: 99%

Stereoselective Desymmetrization of Cyclohexadienone-Tethered Enones: Efficient Access to Highly Strained Polycyclic Indoles

et al. 2019

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A highly regioselective and stereoselective cascade annulation of indoles with C2-symmetric enone tethered-cyclohexadienones provides rapid access to complex indole alkaloid-like scaffolds in high yields. Interestingly, a different reaction course was observed with 3-substituted indoles giving C-2/N annulation products with similar complexity via intramolecular aza-Michael addition. This desymmetrization approach is highly practical and allows atom-economical synthesis of natural product-like molecules containing several contiguous stereocenters with broad range of substrate scope and high functional-group tolerance. The synthetic utility of the products was demonstrated with various chemoselective, regioselective, and diastereoselective transformations on the highly strained polycyclic indoles to elaborate the value of this tandem reaction.

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Scaffold Diversity Synthesis with Branching Cascades Strategy

Cited by 7 publications

References 66 publications

Synthesis of Cyclopropanoids via Substrate-Based Cyclization Pathways

Synthesis of Cyclopropanoids via Substrate-Based Cyclization Pathways

One-Pot Double Intramolecular Cyclization Approach to Tetralin-Based Cis-Fused Tetracyclic Compounds

Stereoselective Desymmetrization of Cyclohexadienone-Tethered Enones: Efficient Access to Highly Strained Polycyclic Indoles

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