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An Efficient Synthesis of Tetrodotoxin

An organic chemistry minilecture on the total synthesis of Tetrodotoxin by David B. Konrad, Klaus-Peter Rühmann, Hiroyasu Ando, Belinda E. Hetzler, Bryan S. Matsuura* and Dirk Trauner*. Highlights include a Bernet-Vasella Fragmentation/ Henry Reaction/ Dehydration Cascade, a nitrile oxide-alkene cycloaddition and a tandem ruthenium-promoted cycloisomerization/ ketohydroxylation oxidation reaction SUPPORT THE CHANNEL ON PATREON:   / simplifyingsynthesis   Socials:   / simplifyingsynthesis     / simplifyingsyn1     / simplifyingsynthesis   References: 10.33774/chemrxiv-2021-xkftp (This work, final version now published in Science 2022, 377, 411–415.) Pure Appl. Chem.  1964, 9 (1): 49–75. (Structure Identification) Mar. Drugs 2011, 9, 2046-2074 (Tetrodotoxin Synthesis Review) J. Org. Chem. 2008, 73, 1234–1242 (Synthesis of glucose derivative) Eur. J. Org. Chem. 2013, 5022–5027 (Bernet-Vasella Fragmentation/ Henry Reaction Cascade) Synthesis 1997, 3, 309-312 (Nitrone cycloaddition) Molander, G. A. (1994). Reductions with Samarium(II) Iodide. Organic Reactions (pp. 211–367) (oxazolidine reduction) J. Org. Lett. 2010, 12, 4, 684–687 (Cycloisomerization) J. Am. Chem. Soc. 1999, 121, 50, 11680–11683 (Cycloisomerization) Org. Lett. 20201, 23, 514–518 (chromoselective photochemical debenzylation) Previous Syntheses of Tetrodotoxin: J. Am. Chem. Soc. 1972, 94, 9219–9221 J. Am. Chem. Soc. 2003, 125, 8798–8805 J. Am. Chem. Soc. 2003, 125, 11510–11511 Angew. Chem. Int. Ed. 2004, 43, 4782–4785 Chem Asian J. 2006 , 125–135 J. Org. Chem. 2005, 70, 7496–7504 J. Org. Chem. 2008, 73, 1234–1242 BCSJ. 2010, 83, 279–287 Guide to Conformational Analysis:    • The Simplifying Synthesis Ultimate Guide T...   0:00 Introduction 0:18 An Efficient Synthesis of Tetrodotoxin 2:27 Tetradotoxin- Challenges 3:14 Retrosynthesis 3:56 Acetal Reduction 4:38 Sharpless Dihydroxylation 5:18 Acetonide Protection 6:02 Appel Reaction 7:28 Michael Addition 9:18 Alkyne Installation 10:12 Protecting Group Manipulation 11:03 Isoxazolidine Reduction 11:25 Hydroxylactonization 14:18 Guanylation 14:49 Oxidation 15:03 Cyclization 16:53 Summary