Chiron approach from D-mannitol to access a diastereomer of the reported structure of an acetogenin, an amide alkaloid and a sex pheromone

Chatterjee, Shankar; Manna, Avrajit; Chakraborty, Ipsita; Bhaumik, Tanurima

doi:10.1016/j.carres.2018.12.008

Cited by 7 publications

(2 citation statements)

References 39 publications

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“…Fig. 9 shows the pheromones of Osmoderma eremita (Col., Cetoniidae): 194, 174,175 Nasonia vitripennis (Hym., Pteromalidae): 195, 176 Bactrocera tsuneonis (Dip., Tephritidae): 196, 177 Popillia japonica (Col., Scarabaeidae): (R)-197 and Anomala osakana (Col., Scarabaeidae): (S)-197, 178 Rhagoletis batava (Dipt., Tephritidae): 198, 179 Macrocentrus grandii (Hym., Braconidae): 199, 180 Vespa orientalis (Hym., Vespidae): 200, [181][182][183][184] Culex spp. (Dip., Culicidae): 201, [185][186][187][188][189] Phoracantha synonyma (Col., Cerambycidae): 202, 190 Silvestritermes minutus (Iso., Termitidae): 203, 191 Heliconius erato phyllis (Lep., Nymphalidae): 204 (anti-aphrodisiac).…”

Section: Reviewmentioning

confidence: 99%

Recent advances in the synthesis of insect pheromones: an overview from 2013 to 2022

et al. 2023

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Section: Reviewmentioning

confidence: 99%

Recent advances in the synthesis of insect pheromones: an overview from 2013 to 2022

et al. 2023

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“…The amide functional group has been widely found in natural products and is the one of most fundamental building blocks . For example, α-amino acids are linked by an amide bond to form protein which is the bedrock of life .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Amides via the Amination of Aldehydes with Hydroxylamines Promoted by TBAF·3H₂O

Zhang,

Xu,

et al. 2024

J. Org. Chem.

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A metal-free, mild, and efficient method for the synthesis of amides has been developed from the amination of aldehydes with hydroxylamines promoted by TBAF·3H2O in the presence of KOH. Control experiments showed that the nitrone was the intermediate of this amination. By this method, a series of amides, biologically active compounds bebenil and a COX inhibitor were obtained in moderate to good yields.

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A Decade of Muricatacin Synthesis and Beyond

et al. 2020

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In this review, we have abstracted the various syntheses of both enantiomers of muricatacin (a member of a bigger class of acetogenins, ACGs), over the last decade (2010–2020). Developments in the synthesis of various epimers, homologues, oxa‐analogues, δ‐lactones, and the furofuranone analogues are also enfolded in this review. Most of the synthesis involve chiral pool and catalytic enantioselective approaches, while a few are hinged on the use of chiral auxiliary and resolution methods. Muricatacin with orthogonally differentiated two oxy‐functions also serve as a start point in the synthesis of higher molecules of the acetogenin family, for example, cis‐solamins, and these have also been covered herein.

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Chiron approach from D-mannitol to access a diastereomer of the reported structure of an acetogenin, an amide alkaloid and a sex pheromone

Cited by 7 publications

References 39 publications

Recent advances in the synthesis of insect pheromones: an overview from 2013 to 2022

Recent advances in the synthesis of insect pheromones: an overview from 2013 to 2022

Synthesis of Amides via the Amination of Aldehydes with Hydroxylamines Promoted by TBAF·3H₂O

A Decade of Muricatacin Synthesis and Beyond

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Chiron approach from D-mannitol to access a diastereomer of the reported structure of an acetogenin, an amide alkaloid and a sex pheromone

Cited by 7 publications

References 39 publications

Recent advances in the synthesis of insect pheromones: an overview from 2013 to 2022

Recent advances in the synthesis of insect pheromones: an overview from 2013 to 2022

Synthesis of Amides via the Amination of Aldehydes with Hydroxylamines Promoted by TBAF·3H2O

A Decade of Muricatacin Synthesis and Beyond

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Product

Resources

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Synthesis of Amides via the Amination of Aldehydes with Hydroxylamines Promoted by TBAF·3H₂O