Strategies for the synthesis of<i>Stemona</i>alkaloids: an update

Olivier, Wesley J.; Henneveld, Jackson S.; Smith, Jason A.; Hawkins, Bill C.; Bissember, Alex C.

doi:10.1039/d2np00058j

Nat. Prod. Rep.

2022

DOI: 10.1039/d2np00058j

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Strategies for the synthesis ofStemonaalkaloids: an update

Wesley J. Olivier

Jackson S. Henneveld

Jason A. Smith

et al.

Abstract: The Stemona alkaloids represent a large and structurally-diverse family of natural products. A selection of case studies are presented to showcase the key strategies and progress in the synthesis of these natural products since 2009.

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Cited by 7 publications

References 154 publications

(145 reference statements)

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A Rapid Bioinspired N‐Acyliminium Ion Strategy for the ABC Core of the Stemona Alkaloids

Chavan,

Kalbhor,

Gonnade

2023

Asian J Org Chem

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A concise and highly diastereoselective bioinspired key cationic cyclization strategy for the asymmetric synthesis of the tricyclic core of the (–)‐stemoamide, together with 8,9‐bis‐epi‐stemoamide has been described. The key N‐acyliminium ion precursors were accessed from L‐tartaric acid and L‐malic acid respectively. The use of ethyl acetoacetate derived bifunctional allylidenetriphenylphosphorane reagent in the early stage of the synthetic strategy is advantageous for the rapid construction of highly functionalized key pyrrolo[1,2‐α]azepine frameworks.

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A Rapid Bioinspired N‐Acyliminium Ion Strategy for the ABC Core of the Stemona Alkaloids

Chavan,

Kalbhor,

Gonnade

2023

Asian J Org Chem

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Chiron approach toward the synthesis of the fused tricyclic core of epi-parvistemonine A

Marín-Cruz,

Tovar-Miranda,

Romero-Ibáñez

et al. 2024

Carbohydrate Research

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Detoxification and underlying mechanisms towards toxic alkaloids by Traditional Chinese Medicine processing: A comprehensive review

Shan,

Yu,

et al. 2024

Phytomedicine

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Strategies for the synthesis ofStemonaalkaloids: an update

Abstract: The Stemona alkaloids represent a large and structurally-diverse family of natural products. A selection of case studies are presented to showcase the key strategies and progress in the synthesis of these natural products since 2009.

Cited by 7 publications

References 154 publications

A Rapid Bioinspired N‐Acyliminium Ion Strategy for the ABC Core of the Stemona Alkaloids

A Rapid Bioinspired N‐Acyliminium Ion Strategy for the ABC Core of the Stemona Alkaloids

Chiron approach toward the synthesis of the fused tricyclic core of epi-parvistemonine A

Detoxification and underlying mechanisms towards toxic alkaloids by Traditional Chinese Medicine processing: A comprehensive review

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