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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH FRONT

A Total Synthesis of the Marine Alkaloid Ningalin B from (S)-Proline

Katrin Hasse A , Anthony C. Willis A and Martin G. Banwell A B
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- Author Affiliations

A Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia.

B Corresponding author. Email: mgb@rsc.anu.edu.au

Australian Journal of Chemistry 62(7) 683-691 https://doi.org/10.1071/CH09158
Submitted: 16 March 2009  Accepted: 12 May 2009   Published: 13 July 2009

Abstract

The title alkaloid 1 has been synthesized from (S)-proline (2) using a sequence of reactions involving oxidative bromination (of 2), N-alkylation, Suzuki–Miyaura cross-coupling, and bromination steps.


Acknowledgements

We thank the Gottlieb Daimler and Karl Benz Foundation for the provision of a PhD stipend to K.H. and the Australian Research Council for a grant (DP0771749).


References


[1]   H. Kang, W. Fenical, J. Org. Chem. 1997, 62,  3254.
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