Abstract
11-Saxitoxinethanoic acid (SEA) is a member of the saxitoxin (STX) family of paralytic shellfish poisons, and contains an unusual C−C bond at the C11 position. Reported herein is a total synthesis of SEA. The key to our synthesis lies in a Mukaiyama aldol condensation reaction of silyl enol ether with glyoxylate in the presence of an anhydrous fluoride reagent, [Bu4N][Ph3SnF2], which directly constructs the crucial C−C bond at the C11 position in SEA. The NaVCh-inhibitory activities of SEA and its derivatives were evaluated by means of cell-based assay. SEA showed an IC50value of (47±12) nm, which is approximately twice as potent as decarbamoyl-STX (dcSTX).
Original language | English |
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Pages (from-to) | 11600-11603 |
Number of pages | 4 |
Journal | Angewandte Chemie - International Edition |
Volume | 55 |
Issue number | 38 |
DOIs | |
Publication status | Published - 2016 Sep 12 |
Keywords
- aldol reaction
- heterocylces
- natural products
- saxitoxin
- total synthesis
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)