Synthesis of the 8-Deoxy Analogue of 4,9-Anhydro-10-hemiketal-5-deoxy-tetrodotoxin, a Proposed Biosynthetic Precursor of Tetrodotoxin
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- Tadachika Miyasaka
- Graduate School of Bioagricultural Sciences, Nagoya University, Nagoya 464-8601, Japan
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- Masaatsu Adachi
- Graduate School of Bioagricultural Sciences, Nagoya University, Nagoya 464-8601, Japan
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- Toshio Nishikawa
- Graduate School of Bioagricultural Sciences, Nagoya University, Nagoya 464-8601, Japan
Description
Despite decades of research, the biosynthesis of tetrodotoxin, also known as a puffer fish toxin, remains an unsolved mystery. We disclose a synthesis of the 8-deoxy analogue of 4,9-anhydro-10-hemiketal-5-deoxy-tetrodotoxin, a possible biosynthetic precursor of tetrodotoxin isolated from the Japanese toxic newt, by an intramolecular radical cyclization of a known starting material.
Journal
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- Organic Letters
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Organic Letters 23 (23), 9232-9236, 2021-11-15
American Chemical Society (ACS)