Chemoenzymatic Synthesis of Advanced Intermediates for Formal Total Syntheses of Tetrodotoxin. Issue 34 (30th May 2018)

• Record Type: Journal Article
• Authors: Baidilov, Daler; Rycek, Lukas; Trant, John F.; Froese, Jordan; Murphy, Brennan; Hudlicky, Tomas
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 34(2018)
• Page Start: 10994
• Page End: 10998
• Publication Date: 2018-05-30
• Subjects: chemoenzymatic synthesis -- formal synthesis -- hydride shift -- tetrodotoxin -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201804602
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Advanced intermediates for the syntheses of tetrodotoxin reported by the groups of Fukuyama, Alonso, and Sato were prepared. Key steps include the toluene dioxygenase mediated dihydroxylation of either iodobenzene or benzyl acetate. The resulting diene diols were transformed into Fukuyama's intermediate in six steps, into Alonso's intermediate in nine steps, and into Sato's intermediate in ten steps. Abstract : Advanced intermediates of the syntheses of tetrodotoxin reported by the groups of Fukuyama, Alonso, and Sato were prepared. Key steps include the toluene dioxygenase mediated dihydroxylation of either iodobenzene or benzyl acetate. The resulting diene diols were transformed into Fukuyama's intermediate in six steps, into Alonso's intermediate in nine steps, and into Sato's intermediate in ten steps.