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.
A concise stereoselective total synthesis of (+)-saxitoxin is described. A n class="Chemical">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.
Authors: Gang Yan; Bereket L Zekarias; Xiaoyu Li; Victor A Jaffett; Ilia A Guzei; Jennifer E Golden Journal: Chemistry Date: 2020-02-06 Impact factor: 5.236
Authors: James R Walker; Jeffrey E Merit; Rhiannon Thomas-Tran; Doris T Y Tang; J Du Bois Journal: Angew Chem Int Ed Engl Date: 2019-01-02 Impact factor: 15.336