Journal of the American Chemical Society, Vol.133, No.50, 20172-20174, 2011
A Stereocontrolled Synthesis of (+)-Saxitoxin
A concise stereoselective total synthesis of (+)-saxitoxin is described. A silver(I)-initiated hydroamination cascade constructs the bicyclic guanidinium ion core from a alkynyl bisguanidine. This sequence creates two C-N bonds, one C-O bond, and three rings and forms a single stereoisomer in a single synthetic transformation. This process enabled us to complete the synthesis of (+)-saxitoxin in 14 steps from N-Boc-L-serine methyl ester.