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- W4313506314 abstract "Tetrodotoxin and congeners are specific voltage-gated sodium channel blockers that exhibit remarkable anesthetic and an-algesic effects. Here, we present a scalable asymmetric synthesis of TTX and 9-epiTTX from the abundant chemical feed-stock furfuryl alcohol. The optically pure cyclohexane skeleton was assembled via a stereoselective Diels-Alder reaction. The dense heteroatom substituents were established sequentially by a series of functional group interconversions on highly oxygenated cyclohexane frameworks, including a chemoselective cyclic anhydride opening, and a decarboxylative hydrox-ylation. An innovative SmI2-mediated concurrent fragmentation, an oxo-bridge ring opening and ester reduction followed by an Upjohn dihydroxylation delivered the highly oxidized skeleton. Ruthenium-catalyzed oxidative alkyne cleavage and formation of the hemiaminal and orthoester under acidic conditions enabled the rapid assembly of TTX, anhydro-TTX, 9-epiTTX, and 9-epi lactone-TTX." @default.
- W4313506314 created "2023-01-06" @default.
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- W4313506314 date "2023-01-04" @default.
- W4313506314 modified "2023-10-17" @default.
- W4313506314 title "Total Synthesis of Tetrodotoxin and 9-epiTetrodotoxin" @default.
- W4313506314 doi "https://doi.org/10.26434/chemrxiv-2023-76wll-v2" @default.
- W4313506314 hasPublicationYear "2023" @default.
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