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.
Marco Bandini; Michele Contento; Andrea Garelli; Magda Monari; Alessandra Tolomelli; Achille Umani-Ronchi; Erika Andriolo; Mauro Montorsi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/64899
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