Journal article
Total Synthesis of (−)-Spiroleucettadine
RA Lamb, NS Aberle, NT Lucas, G Lessene, BC Hawkins
Angewandte Chemie International Edition | WILEY-V C H VERLAG GMBH | Published : 2017
Abstract
One of a number of intriguing new alkaloids isolated from the Leucetta sp. sponge in 2004, spiroleucettadine displayed unique structural features on a restricted scaffold: a trans-fused 5,5-bicyclic ring system together with an amino hemiketal moiety. Attempts to synthesize the initially proposed structure failed, raising questions as to its veracity, and structure revision ensued in 2008; no successful synthetic approach has been reported to date. Herein, we describe the enantiospecific total synthesis of (−)-spiroleucettadine by a highly efficient biomimetic approach starting from l-tyrosine. One of two key hypervalent-iodine-mediated oxidation reactions forged the spirocyclic center, and ..
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Awarded by National Health and Medical Research Council
Funding Acknowledgements
We thank Assoc. Prof. Gareth Rowlands and Prof. Shane Telfer (Massey University) for helpful discussions and Prof. Geoff Jameson (Massey University) for providing dl-tyrosine. Support for this research from the NHMRC (fellowship for G.L. GNT1117089), the Australian Cancer Research Foundation, the Victorian State Government Operational Infrastructure Support, and Australian Government NHMRC IRIISS is gratefully acknowledged.