Abstract
Several isoxazolidines, derived from the 1,3-dipolar cycloaddition of α,β-hexenolides to cyclic nitrones, were converted into the corresponding piperidine- and pyrrolidine-oxepinones by reduction of the nitrogen-oxygen bond. The potential of the resulting amino alcohols as synthetic precursors of polycyclic alkaloids was explored. These intermediates provide a new access to the 1-azabicyclo[5.3.0]decane core of the Sfemona alkaloids. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Original language | English |
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Pages (from-to) | 4215-4233 |
Journal | European Journal of Organic Chemistry |
Issue number | 20 |
DOIs | |
Publication status | Published - 11 Oct 2004 |
Keywords
- Isoxazolidine
- Oxepinone
- Piperidine
- Polycyclic alkaloids
- Pyrrolidine
- Stemona