Biomimetic approach to Galbulimina type I alkaloids

Tchabanenko, K., Chesworth, R., Parker, J. S., Anand, N. K., Russell, A. T., Adlington, R. M. and Baldwin, J. E. (2005) Biomimetic approach to Galbulimina type I alkaloids. Tetrahedron, 61 (49). pp. 11649-11656. ISSN 0040-4020 doi: 10.1016/j.tet.2005.09.050

Abstract/Summary

On treatment with trifluoroacetic acid the tetraene precursor 23 underwent Boc deprotection, condensation and an iminium ion accelerated intramolecular Diels-Alder cycloaddition resulting in an iminium species 12, which was further converted into himbacine 1, himbeline 3 and himandravine 4, three out of four Galbulimina type I alkaloids thus providing strong evidence for the proposed biogenesis of this important family of alkaloids.