Synthesis of the tricyclic core of manzamine A.


An efficient synthetic approach to the core structure of the manzamine alkaloids is reported, particularly in relation to incorporating a one-carbon unit in ring B from which the aldehyde in ircinal A or the beta-carboline unit in manzamine A could potentially be generated. The key steps involve a Johnson-Claisen rearrangement, enolate alkylation, dithiane alkylation and a stereoselective intramolecular dipolar cycloaddition of an azomethine ylide, which provided the desired tricyclic ABC core structure.

DOI: 10.1039/c4ob02582b

Cite this paper

@article{Pathak2015SynthesisOT, title={Synthesis of the tricyclic core of manzamine A.}, author={Ravindra B. Pathak and Benjamin C Dobson and Nandita Ghosh and Khalid A Ageel and Madeha R Alshawish and Rungroj Saruengkhanphasit and Iain Coldham}, journal={Organic & biomolecular chemistry}, year={2015}, volume={13 11}, pages={3331-40} }