ORGN 529 |
Synthetic studies toward the paralytic shellfish poison (+)-saxitoxin
| James J. Fleming and Justin Du Bois. Department of Chemistry, Stanford University, Stanford, CA 94305 |
| One area of ongoing research in our group is the synthesis of neuroactive natural products for the development of new pharmacological tools. (+)-Saxitoxin (STX) has been recognized as one of the most toxic non-protein substances known to date. First isolated in 1957, STX is the active component of paralytic shellfish poisoning observed during red tide outbreaks. The remarkable physiological activity demonstrated by this molecule results from its ability to bind tightly the voltage-gated sodium channel. Given its demanding structure the efficient asymmetic synthesis of saxitoxin presents an ideal challenge for the development of new stereoselective bond forming processes. Our research efforts toward the target molecule and the advances in methodology made during these investigations will be discussed. At the center of our strategy is the discovery of a novel class of iminium ion equivalents for the rapid construction of stereochemically defined propargylic amine derivatives. 
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