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 / Marco Bandini; Michele Contento; Andrea Garelli; Magda Monari; Alessandra Tolomelli; Achille Umani-Ronchi; Erika Andriolo; Mauro Montorsi. - In: SYNTHESIS. - ISSN 0039-7881. - STAMPA. - 23:(2008), pp. 3801-3804. [10.1055/s-0028-1087226]
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
