A chemoenzymatic route to the (+)-form of the amaryllidaceae alkaloid narseronine

Shuxin Yang; Martin G. Banwell; Anthony C. Willis; Jas S. Ward

doi:10.1071/CH14520

A chemoenzymatic route to the (+)-form of the amaryllidaceae alkaloid narseronine

Shuxin Yang, Martin G. Banwell^*, Anthony C. Willis, Jas S. Ward

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

The enzymatically derived and enantiopure cis-1,2-dihydrocatechol 1 has been converted, over 14 one-pot operations, into the (+)-form of the alkaloid narseronine (2). The present study, which complements earlier work that established a route from metabolite 1 to enantiomer (-)-2, involves an N-bromosuccinimide/tri-n-butyltin hydride-mediated cyclisation reaction to construct the unsaturated B-ring lactone of the target compound.

Original language	English
Pages (from-to)	241-247
Number of pages	7
Journal	Australian Journal of Chemistry
Volume	68
Issue number	2
DOIs	https://doi.org/10.1071/CH14520
Publication status	Published - 2015

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10.1071/CH14520

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abstract = "The enzymatically derived and enantiopure cis-1,2-dihydrocatechol 1 has been converted, over 14 one-pot operations, into the (+)-form of the alkaloid narseronine (2). The present study, which complements earlier work that established a route from metabolite 1 to enantiomer (-)-2, involves an N-bromosuccinimide/tri-n-butyltin hydride-mediated cyclisation reaction to construct the unsaturated B-ring lactone of the target compound.",

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AU - Ward, Jas S.

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AB - The enzymatically derived and enantiopure cis-1,2-dihydrocatechol 1 has been converted, over 14 one-pot operations, into the (+)-form of the alkaloid narseronine (2). The present study, which complements earlier work that established a route from metabolite 1 to enantiomer (-)-2, involves an N-bromosuccinimide/tri-n-butyltin hydride-mediated cyclisation reaction to construct the unsaturated B-ring lactone of the target compound.

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JO - Australian Journal of Chemistry

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A chemoenzymatic route to the (+)-form of the amaryllidaceae alkaloid narseronine

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