First Total Synthesis of (-)-Fumitremorgin C |
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| Affiliation: | 1. Department of Pharmaceutical Sciences, Leslie Dan Faculty of Pharmacy, University of Toronto, Toronto, Ontario, Canada;2. Centre for Probe Development and Commercialization (CPDC), McMaster University, Hamilton, Ontario, Canada;3. Department of Chemistry and Chemical Biology, McMaster University, Hamilton, Ontario, Canada |
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| Abstract: | The first total synthesis of the tremorgic mycotoxin furnitremorgin C (1a) employing 6-methoxy-N-hydroxytryptophan (5a) is presented. Our approach features formation of the nitrone (6a), stereoselective cycloaddition to yield 7a, ring opening and coupling with an L-proline derivative to form 14. Base-catalysed epimerisation gave 16, which was converted into the title compound by deprotection of the amine function, dioxopiperazine formation and dehydration. |
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