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S1 ELECTRONIC SUPPLEMENTARY INFORMATION FOR: 3,4'-Linked bis(piperidines) related to the haliclonacyclamine class of marine alkaloids: synthesis using crossed-aldol chemistry and preliminary biological evaluations Martin G. Banwell, a * Mark J. Coster, a Natasha L. Hungerford, a Mary J. Garson, b Stephen Su, c Andrew C. Kotze d and Murray H. G. Munro e a Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia. E-mail: [email protected] b School of Chemistry and Molecular Biosciences, The University of Queensland, St Lucia, QLD 4072, Australia. c Cytopia Pty Ltd, 576 Swan St, Richmond, VIC 3121, Australia. d CSIRO Livestock Industries, Queensland Bioscience Precinct, Brisbane, QLD 4067, Australia. e Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch, New Zealand. Contents Page 1 H and/or 13 C NMR Spectra of Compounds 25, and 710 S2–S17 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2011

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ELECTRONIC SUPPLEMENTARY INFORMATION FOR:

3,4'-Linked bis(piperidines) related to the haliclonacyclamine class of marine alkaloids: synthesis using crossed-aldol chemistry and preliminary biological evaluations Martin G. Banwell,a* Mark J. Coster,a Natasha L. Hungerford,a Mary J. Garson,b Stephen Su,c Andrew C. Kotzed and Murray H. G. Munroe aResearch School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia. E-mail: [email protected] bSchool of Chemistry and Molecular Biosciences, The University of Queensland, St Lucia, QLD 4072, Australia. cCytopia Pty Ltd, 576 Swan St, Richmond, VIC 3121, Australia. dCSIRO Livestock Industries, Queensland Bioscience Precinct, Brisbane, QLD 4067, Australia. eDepartment of Chemistry, University of Canterbury, Private Bag 4800, Christchurch, New Zealand.

Contents Page

1H and/or 13C NMR Spectra of Compounds 2–5, and 7–10 S2–S17

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011