A new synthetic approach for the construction of the spirolactone moiety of the progestin drospirenone is presented. Highly efficient cross-metathesis reaction catalyzed by Grubbs-Hoveyda second generation catalyst (6 mol%) is employed as the key step for the introduction of the ester moiety in the position C-17. The no need for protecting groups and the absence of harmful heavy metal-based oxidants constitute a valuable synthetic alternative to the existent approaches.
A Nonclassical Stereoselective Semi-Synthesis of Drospirenone via Cross-Metathesis Reaction
BANDINI, MARCO;CONTENTO, MICHELE;GARELLI, ANDREA;MONARI, MAGDA;TOLOMELLI, ALESSANDRA;UMANI RONCHI, ACHILLE;
2008
Abstract
A new synthetic approach for the construction of the spirolactone moiety of the progestin drospirenone is presented. Highly efficient cross-metathesis reaction catalyzed by Grubbs-Hoveyda second generation catalyst (6 mol%) is employed as the key step for the introduction of the ester moiety in the position C-17. The no need for protecting groups and the absence of harmful heavy metal-based oxidants constitute a valuable synthetic alternative to the existent approaches.File in questo prodotto:
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