An Acylnitroso Cycloaddition Approach to the Synthesis of Highly Oxygenated Indolizidine Alkaloids

Article abstract of DOI:10.1021/jo00074a040

A synthetic approach to the synthesis of highly oxygenated indolizidine alkaloids is described.A key feature of the approach is intramolecular <4 + 2> cycloaddition between an acylnitroso dienophile and a tethered diene moiety, followed by ring contraction of the 1,2-oxazine so formed to a pyrrolidine.The requisite intermediates were prepared in optically pure form from L-glutamic acid.