Chemoenzymatic Synthesis of Advanced Intermediates for Formal Total Syntheses of Tetrodotoxin. (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. Volume 130:Number 34(2018)
• Page Start: 11160
• Page End: 11164
• Publication Date: 2018-05-30
• Subjects: Chemoenzymatische Synthesen -- Formale Synthesen -- Hydridverschiebung -- Tetrodotoxin -- Totalsynthesen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201804602
• Languages: English
• ISSNs: 0044-8249

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.