2011/11/18 by Vasudev R. Bhonde, Ryan Looper · 1 citation
Environmental Science · Biochemistry, Genetics and Molecular Biology · Chemistry · #Marine Toxins and Detection Methods #Marine Sponges and Natural Products #Oxidative Organic Chemistry Reactions
paper · doi:10.1021/ja2098063
openalex publication_date 2011/11/18 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01
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.