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RESEARCH ARTICLE
Contents Vol 70(3)

Sweet Poisons: Synthetic Strategies towards Tutin Glycosides

Duong Nhu A , Lesley Larsen A B , Nigel B. Perry A B , David S. Larsen A and Bill C. Hawkins A C
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, University of Otago, PO Box 56, Dunedin 9054, New Zealand.

B The New Zealand Institute for Plant and Food Research Limited, Department of Chemistry, University of Otago, PO Box 56, Dunedin 9054, New Zealand.

C Corresponding author. Email: bhawkins@chemistry.otago.ac.nz

Australian Journal of Chemistry 70(3) 301-306 https://doi.org/10.1071/CH16429
Submitted: 22 July 2016  Accepted: 23 August 2016   Published: 15 September 2016

Abstract

The polycyclic, polyoxygenated picrotoxane tutin was subjected to various glycosylation reaction conditions in an effort to synthesise β-linked tutin glycosides, recently found in toxic honeys. Cationic palladium-mediated glycosylation of tutin was successful; however, the α-linked tutin tetrabenzyl glucoside was obtained as the major product (5 : 1, α : β). Hydrogenolysis of the benzyl ether protecting groups resulted in concomitant tutin double-bond migration. Epoxide opening and rearrangement were observed upon acetylation of the tutin glucoside.


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