The Absolute Configurations of Haliclonacyclamines A and B Determined by X-Ray Crystallographic Analysis

I. Wayan Mudianta; Mary J. Garson; Paul V. Bernhardt

doi:10.1071/CH09128

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The Absolute Configurations of Haliclonacyclamines A and B Determined by X-Ray Crystallographic Analysis

I. Wayan Mudianta ^A ^B , Mary J. Garson ^A ^C and Paul V. Bernhardt ^A ^C

+ Author Affiliations

- Author Affiliations

^A School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, QLD 4072, Australia.

^B Department of Analytical Chemistry, Faculty of Mathematics and Natural Sciences Education, Ganesha University of Education, Bali 81117, Indonesia.

^C Corresponding authors. Email: m.garson@uq.edu.au; p.bernhardt@uq.edu.au

Australian Journal of Chemistry 62(7) 667-670 https://doi.org/10.1071/CH09128
Submitted: 4 March 2009 Accepted: 1 April 2009 Published: 13 July 2009

Abstract

X-Ray crystallography establishes that the marine alkaloids (–)-haliclonacyclamine A 1 and (+)-haliclonacyclamine B 2 each have the configuration C2 (R), C3 (R), C7 (R), and C9 (R). The alkaloids appear to be enantiomerically pure; this provides an insight into the stereochemical consequences of the biosynthetic pathway leading to these bioactive 3-alkylpiperidine alkaloids.

Acknowledgements

We thank the Australian Research Council, the School of Chemistry and Molecular Biosciences and The University of Queensland for financial support, and AusAID for an Indonesian Development Scholarship (to I.W.M.). The assistance of Dr Tri Le (NMR) and Graham McFarlane (MS), and of staff from Heron Island Research Station (collection of sponge samples) is gratefully acknowledged. Permission to collect sponge samples was provided by Great Barrier Reef Marine Park Authority.

References

The Absolute Configurations of Haliclonacyclamines A and B Determined by X-Ray Crystallographic Analysis

Abstract

Acknowledgements

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