Chiron approach for the synthesis of (5RS)-Hagen’s gland lactones from diacetone-d-mannose |
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| Affiliation: | 1. Faculty of Environmental Sciences, Czech University of Life Sciences, Prague, Czech Republic;2. University of Chemistry and Technology, Prague, Czech Republic |
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| Abstract: | A new and convergent synthetic route for (5RS)-Hagen’s lactones 1–4 is described, starting from bisacetonide mannofuranolactone 5. The key transformations in the synthesis are SmI2 mediated α-deoxygenation of a aldonolactone to 2-deoxy lactone, Pd(II) mediated oxidative cyclization and an oxidation of tetrahydrofuran to a furanone. |
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