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A Stereocontrolled Synthesis of (+)-Saxitoxin

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journal contribution
posted on 2011-12-21, 00:00 authored by Vasudev R. Bhonde, Ryan E. Looper
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.

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