1333080-62-8Relevant articles and documents
Gold(I)-catalysed intramolecular hydroamination of α-quaternary alkynes: Synthetic studies towards spiroimine marine toxins
Zhang, Yanchuan C.,Furkert, Daniel P.,Guéret, Stéphanie M.,Lombard, Fanny,Brimble, Margaret A.
, p. 4896 - 4898 (2011/10/05)
Cyclic spiroimines form an essential component of the bioactive pharmacophore in a number of potent fast-acting marine biotoxins, including the pinnatoxins, gymnodimine and the spirolides. These present a significant challenge for the total synthesis of this class of natural products. A novel approach to these cyclic spiroimines based on metal-catalysed hydroamination of spiroaminoalkyne precursors is reported herein. Au(PPh3)SbF 6 was found to effect the formation of bench-stable 5,6- and 6,6-spiroimine systems in high yields, although the 7,6-analogue remained elusive. To the best of our knowledge these are the first reported examples of α-quaternary cyclic imines formed via alkyne hydroamination.
