Evolution of a Strategy for the Enantioselective Synthesis of (−)-Cajanusine

Guo, Renyu; Witherspoon, Brittany P.; Brown, M. Kevin

doi:10.1021/jacs.0c00359

Cited by 22 publications

(20 citation statements)

References 38 publications

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“…In 2020, Brown and co‐workers reported an enantioselective synthesis of (−)‐cajanusine ( 365 , Scheme 39). [72] The asymmetric intramolecular [2+2]‐cycloaddition reaction of 357 catalyzed by the quinine thiourea catalyst ( 358 ) led to the formation of an intermediate, which, upon the treatment with Bi(OTf) 3 in situ, yielded the bicyclic compound 359 . Compound 359 contains the same skeleton as the desired natural product and served as the key intermediate of the total synthesis.…”

Section: Applications In Natural Product Synthesismentioning

confidence: 99%

“…Further synthetic maneuvers on this intermediate led to the successful synthesis of (−)‐cajanusine ( 365 , Scheme 39). [72] …”

Section: Applications In Natural Product Synthesismentioning

confidence: 99%

“…[71] In 2020, Brown and co-workers reported an enantioselective synthesis of (À )-cajanusine (365, Scheme 39). [72] The asymmetric intramolecular [ served as the key intermediate of the total synthesis. Further synthetic maneuvers on this intermediate led to the successful synthesis of (À )-cajanusine (365, Scheme 39).…”

Section: Bifunctional Organocatalystsmentioning

confidence: 99%

“…Further synthetic maneuvers on this intermediate led to the successful synthesis of (À )-cajanusine (365, Scheme 39). [72] In 2016, Zhu and co-workers developed a highly efficient asymmetric total synthesis of (+)-peganumine A (372, Scheme 40). [73] They first developed a novel strategy to access the tetracyclic α-ketolactam 366.…”

Section: Bifunctional Organocatalystsmentioning

confidence: 99%

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Recent Applications of Asymmetric Organocatalytic Methods in Total Synthesis

2021

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Natural products are the great sources of drugs and leading compounds in drug discovery, as it has been estimated that most of the current medicines are derived from natural products. Total synthesis of natural products, especially those of biological activities, has been an important part of organic chemistry, which, besides its potential practical utilities, also provides new inspirations and novel synthetic methodologies. Over the past two decades, organocatalysis has been shown to be very effective in controlling the stereochemistry of the reaction products and has found many applications in the asymmetric synthesis of natural products and related compounds. In this review we will attempt to summarize some applications of asymmetric organocatalysis in the total synthesis of natural products and related compounds in the past seven years.

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Section: Applications In Natural Product Synthesismentioning

confidence: 99%

“…Further synthetic maneuvers on this intermediate led to the successful synthesis of (−)‐cajanusine ( 365 , Scheme 39). [72] …”

Section: Applications In Natural Product Synthesismentioning

confidence: 99%

Section: Bifunctional Organocatalystsmentioning

confidence: 99%

Section: Bifunctional Organocatalystsmentioning

confidence: 99%

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Recent Applications of Asymmetric Organocatalytic Methods in Total Synthesis

2021

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“…[5,6] Although recent advances have given rise to elegant enantioselective methods, the enantioselective synthesis of cyclobutanes is still challenging. [7][8][9][10][11][12] Among the established methods, Lewis acid catalyzed [2+2] cycloaddition between activated olefins and alkenes is particularly interesting because the resulting donor-acceptor cyclobutanes can behave as 1,4-zwitterionic synthons in chemical transformations. [3] In 1989, the Narasaka group reported the first catalytic enantioselective [2+2] cycloadditions using a Ti-TADDOL complex as the catalyst with 1,1bis(methylthio)ethylene as the substrate, and the reaction provided excellent enantioselectivity.…”

mentioning

confidence: 99%

Catalytic Enantioselective [2+2] Cycloaddition of α‐Halo Acroleins: Construction of Cyclobutanes Containing Two Tetrasubstituted Stereocenters

Gao

Zeng

et al. 2020

Angewandte Chemie

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A catalytic enantioselective formal [2+2] cycloaddition between a-halo acroleins and electronically diverse arylalkenes is described. In the presence of (S)-oxazaborolidinium cation as the catalyst, densely functionalized cyclobutanes containing two vicinal tetrasubstituted stereocenters were produced in high yields and high diastereoselectivities with excellent enantioselectivities. Mechanistic studies revealed that the cis isomer could be transformed into the trans isomer via an enantiocontrolled process. A gram-scale reaction of this catalytic method was used to demonstrate its synthetic potential. Scheme 1. Chiral Lewis acid catalyzed asymmetric [2+2] cycloadditions.

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Highlighting the Rich Chemistry of the Allenone Moiety

Almendros

Alonso

2023

Adv Synth Catal

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Conjugated and non-conjugated allenones appear as recurring motifs in organic synthesis, natural products and mechanistic investigations showing unique properties and applications. The ability of allenones to build cycles has provided a direct access to strained systems, medium-sized rings, arenes, heterocycles and complex polycycles. In addition, allenones have served as models in mechanistic investigations and catalysis. The critic compilation herein presented will provide an exhaustive overview of the synthetic possibilities allenones may offer, which certainly will inspire our community in their search of more efficient synthetic methodologies, preparation of biological and pharmaceutical targets, and improve our knowledge in theoretical organic chemistry. Great part of this review will discuss synthetic aspects, catalysis innovation and mechanistic insights of the chemical transformations implying the allenone motif. In addition, many examples on total synthesis and pharmacologically active compounds will be described. We hope that this overview will be attractive to the organic chemistry, synthetic chemistry, catalysis, theoretical chemistry, natural products and medicinal chemistry communities. 3.5. Synthesis of Spirocycles and Bridged Structures 3.6. Open-Chain Structures from Allenones 3.7. Allenones in Total Synthesis 4.

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Evolution of a Strategy for the Enantioselective Synthesis of (−)-Cajanusine

Cited by 22 publications

References 38 publications

Recent Applications of Asymmetric Organocatalytic Methods in Total Synthesis

Recent Applications of Asymmetric Organocatalytic Methods in Total Synthesis

Catalytic Enantioselective [2+2] Cycloaddition of α‐Halo Acroleins: Construction of Cyclobutanes Containing Two Tetrasubstituted Stereocenters

Highlighting the Rich Chemistry of the Allenone Moiety

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