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| | Molecule of the Month: SAXITOXIN |
 | | Saxitoxin is about 1000 times more toxic than a typical synthetic nerve gas such as sarin, and it is perhaps not surprising that in the 1950s, the |
 | | Cyclisation to provide the saxitoxin skeleton was accomplished readily by treatment with acid, the reaction proceeding via the intermediacy of an iminium ion. |
 | | The key step of Jacobi's synthesis of saxitoxin relied on formation of a benzylhydrazide intermediate, which was subjected to methyl glyoxylate hemimethyl acetal and a Lewis acid, in order to construct a highly reactive azomethine imine, which subsequently underwent an intramolecular 1,3-dipolar cycloaddition reaction, leading to an advanced tetracyclic intermediate. |
| www.bris.ac.uk /Depts/Chemistry/MOTM/stx/saxi1.htm (775 words) |
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