Asymmetric Total Synthesis of (−)-Leuconoxine via Chiral Phosphoric Acid Catalyzed Desymmetrization of a Prochiral Diester

Higuchi, Kazuhiro; Suzuki, Shin; Ueda, Reeko; Oshima, Norifumi; Kobayashi, Emiko; Tayu, Masanori; Kawasaki, Tomomi

doi:10.1021/ol5033865

Cited by 45 publications

(21 citation statements)

References 31 publications

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“…In another study, Higuchi et al. detected a hidden symmetry in the structure of (−)‐leuconoxine 145 (Scheme ) . This observation led the authors to envision a desymmetrizing synthesis as a suited strategy to reach 145 .…”

Section: Enantioselective Nucleophilic Substitutionssupporting

confidence: 91%

Enantioselective Brønsted Acid Catalysis as a Tool for the Synthesis of Natural Products and Pharmaceuticals

Merad

Lalli

Bernadat³

et al. 2017

Chemistry A European J

153

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Synthesis of biologically active molecules (whether at laboratory or industrial scale) remains a highly appealing area of modern organic chemistry. Nowadays, the need to access original bioactive scaffolds goes together with the desire to improve synthetic efficiency, while reducing the environmental footprint of chemical activities. Long neglected in the field of total synthesis, enantioselective organocatalysis has recently emerged as an environmentally friendly and indispensable tool for the construction of relevant bioactive molecules. Notably, enantioselective Brønsted acid catalysis has offered new opportunities in terms of both retrosynthetic disconnections and controlling stereoselectivity. The present report attempts to provide an overview of enantioselective total or formal syntheses designed around Brønsted acid-catalyzed transformations. To demonstrate the versatility of the reactions promoted and the diversity of the accessible motifs, this Minireview draws a systematic parallel between methods and retrosynthetic analysis. The manuscript is organized according to the main reaction types and the nature of newly-formed bonds.

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Section: Enantioselective Nucleophilic Substitutionssupporting

confidence: 91%

Enantioselective Brønsted Acid Catalysis as a Tool for the Synthesis of Natural Products and Pharmaceuticals

Merad

Lalli

Bernadat³

et al. 2017

Chemistry A European J

153

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“…Importantly,s uch indolone motifs are found in ar ange of indole alkaloids [4] and are valuablei ntermediates in the total synthesis of related natural products. [5] Over the last decade, photoredox catalysis has emerged as a powerfult ool for organics ynthesis allowingf or the generation of reactive free radical speciesu nder mild conditions and from simple precursors. [6] Notably,photoredox catalysis can be an efficientt ool fori ndole functionalization.…”

Section: In Memory Of Rolf Huisgenmentioning

confidence: 99%

Photocatalytic Synthesis of Polycyclic Indolones

Saget

König

2020

Chemistry A European J

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“…243 In this case, a VAPOL-based phosphoric acid could be used to achieve good enantioselectivity at elevated temperature. 243 In this case, a VAPOL-based phosphoric acid could be used to achieve good enantioselectivity at elevated temperature.…”

Section: Diacids and Diestersmentioning

confidence: 99%

Organocatalytic enantioselective desymmetrisation

et al. 2016

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Organocatalytic enantioselective desymmetrisation of achiral or meso compounds is a powerful strategy for the construction of enantiomerically enriched complex molecules, often with multiple stereocentres and in high selectivities. Recent years have seen increasing use of organocatalysts in desymmetrisation methodology, in contrast to traditional metal- or enzyme-catalysed reactions, with many impressive advances made in the current decade. This review will provide an overview of the field since 2010, with the aim of highlighting both the practical applications and elegance of enantioselective desymmetrisation to the wider synthetic community.

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Asymmetric Total Synthesis of (−)-Leuconoxine via Chiral Phosphoric Acid Catalyzed Desymmetrization of a Prochiral Diester

Cited by 45 publications

References 31 publications

Enantioselective Brønsted Acid Catalysis as a Tool for the Synthesis of Natural Products and Pharmaceuticals

Enantioselective Brønsted Acid Catalysis as a Tool for the Synthesis of Natural Products and Pharmaceuticals

Photocatalytic Synthesis of Polycyclic Indolones

Organocatalytic enantioselective desymmetrisation

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