Formal Total Synthesis of Brevisamide by Using a Tandem Isomerization/C–O and C–C Bond Formation Reaction

Banoth, Shivalal; Maity, Saurabh; Kumar, Sudheer R.; Yadav, J. S.; Mohapatra, Debendra K.

doi:10.1002/ejoc.201600142

Cited by 4 publications

(1 citation statement)

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“…Brevisamide ( 121.4 ), a monocyclic ether alkaloid isolated by Wright and colleagues from the dinoflagellate Karenia brevis , has a trisubstituted ( E,E )‐diene side chain along with a functionalized tetrahydropyran core. Banoth et al [133] . used a two‐step sequence to prepare aldehyde 121.1 from 1,4‐butanediol as a key synthon for the brevisamide synthesis.…”

Section: Thiazolidinethione Chiral Auxiliaries In Asymmetric Synthesismentioning

confidence: 99%

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

2021

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Nature is incessantly affianced to construct bioactive and structurally intriguing compounds with magnificent three‐dimensional frameworks in the Universe. The inadequacy of these naturally occurring precious compounds prompted several minds of chemists to synthesise them in a laboratory for a thorough evaluation of their medicinal and clinical properties via a structure‐activity relationship study. Finding an optimised methodology to synthesise chiral natural products has always been challenging in synthetic organic chemistry, particularly the formation of asymmetric carbon‐carbon bonds adhering to the existing stereochemistry. In this context, chiral auxiliaries have proven to be effective tools for inducing chirality during the synthesis of chiral molecules. In fact, the chiral auxiliary will allow us to control the synthesis of many enantiomerically pure isomers in natural product synthesis. In this area, the significant contribution of the Evans’ chiral auxiliary in TiCl4‐mediated asymmetric aldol reactions to the installation of known configurations in organic synthetic chemistry motivated us to compile an exhaustive and systematic summary of the relevant research findings published in the last two decades.

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Section: Thiazolidinethione Chiral Auxiliaries In Asymmetric Synthesismentioning

confidence: 99%

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

2021

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General Asymmetric Synthetic Strategy for the α‐Alkylated 2,5,6‐Trisubstituted Pyran of Indanomycin and Related Natural Products

et al. 2020

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A general synthetic strategy for convergent asymmetric synthesis of C1–C10 fragment of tetraene‐containing natural product indanomycin was achieved starting from 2‐(benzyloxy)acetaldehyde which in turn was obtained from very inexpensive material cis‐1,4‐butene‐diol. Key steps include Evans' aldol reaction, HWE olefination, iodine‐catalyzed tandem isomerization followed by C–O and C–C bond formation similar to our earlier report in constructing the trans‐2,6‐disubstituted dihydropyran ring and Evans' asymmetric alkylation.

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Six-Membered Ring Systems

Santos¹,

Silva²

2017

Progress in Heterocyclic Chemistry

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Formal Total Synthesis of Brevisamide by Using a Tandem Isomerization/C–O and C–C Bond Formation Reaction

Cited by 4 publications

References 38 publications

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

General Asymmetric Synthetic Strategy for the α‐Alkylated 2,5,6‐Trisubstituted Pyran of Indanomycin and Related Natural Products

Six-Membered Ring Systems

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Formal Total Synthesis of Brevisamide by Using a Tandem Isomerization/C–O and C–C Bond Formation Reaction

Cited by 4 publications

References 38 publications

TiCl4‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

TiCl4‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

General Asymmetric Synthetic Strategy for the α‐Alkylated 2,5,6‐Trisubstituted Pyran of Indanomycin and Related Natural Products

Six-Membered Ring Systems

Contact Info

Product

Resources

About

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis