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Contents Vol 68(2)

A Chemoenzymatic Route to the (+)-Form of the Amaryllidaceae Alkaloid Narseronine*

Shuxin Yang A , Martin G. Banwell A B , Anthony C. Willis A and Jas S. Ward A
+ Author Affiliations
- Author Affiliations

A Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 2601, Australia.

B Corresponding author. Email: martin.banwell@anu.edu.au

Australian Journal of Chemistry 68(2) 241-247 https://doi.org/10.1071/CH14520
Submitted: 26 August 2014  Accepted: 7 September 2014   Published: 3 November 2014

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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