A stereocontrolled synthesis of (+)-saxitoxin |
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Authors: | Bhonde Vasudev R Looper Ryan E |
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Affiliation: | Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, USA. |
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Abstract: | 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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