Optimization of a strategy providing the enantiomericaUy pure nitrone 2 in five steps and 28% overall yield from L-malic acid has been achieved by the combined use of DIBAL-H as the reduftant and triisopropylsilyi as the protecting group. The utility of nitrone 2 as synthetic intermediate is demonstrated by a ready access to polyhydroxylated indolizidinas and pyrrolizidines via stereosclcetive 1,3-dipolar eycloaddition reactions.
A Convenient Access to (3S)-3-(Triisopropyl)oxy-1-pyrroline N-Oxides, a Useful Intermediate for Polyfunctionalized Enantiopure Indolizidine and Pyrrolizidine Synthesis / A. Goti; M. Cacciarini; F. Cardona; A. Brandi. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 40:(1999), pp. 2853-2856. [10.1016/S0040-4039(99)00310-X]
A Convenient Access to (3S)-3-(Triisopropyl)oxy-1-pyrroline N-Oxides, a Useful Intermediate for Polyfunctionalized Enantiopure Indolizidine and Pyrrolizidine Synthesis
GOTI, ANDREA;CACCIARINI, MARTINA;CARDONA, FRANCESCA;BRANDI, ALBERTO
1999
Abstract
Optimization of a strategy providing the enantiomericaUy pure nitrone 2 in five steps and 28% overall yield from L-malic acid has been achieved by the combined use of DIBAL-H as the reduftant and triisopropylsilyi as the protecting group. The utility of nitrone 2 as synthetic intermediate is demonstrated by a ready access to polyhydroxylated indolizidinas and pyrrolizidines via stereosclcetive 1,3-dipolar eycloaddition reactions.
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