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, et al. (2008). A Nonclassical Stereoselective Semi-Synthesis of Drospirenone via Cross-Metathesis Reaction. SYNTHESIS, 23, 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.
