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

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Date

2014-11-03

Authors

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

Journal Title

Journal ISSN

Volume Title

Publisher

CSIRO Publishing

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.

Description

Keywords

Alkaloids, Cyclization, Enzyme activity, Nitrogen compounds, Amaryllidaceae alkaloids, Chemoenzymatic route, Enantiopure, N-bromosuccinimide, One pot, Target compound, Metabolites

Citation

URI

http://hdl.handle.net/1885/13430

Collections

ANU Research Publications

Source

Australian Journal of Chemistry

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

10.1071/CH14520

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