A stereocontrolled synthesis of (+)-saxitoxin.

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.

SUBMITTER: Bhonde VR 

PROVIDER: S-EPMC3320040 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature