A streamlined synthesis of androstadiene C-17 ester derivatives.

Fabrice Gallou, Manuela Seeger-Weibel, Daniel Lupp

Chemical and Analytical Development, Novartis Pharma AG, CHBS, WSJ-145.7.52, Novartis Campus, CH-4056 Basel, Switzerland. fabrice.gallou@novartis.com

Chimia 2011

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The development of a fully telescoped synthesis of a derivative of androstadiene C-17 esters made from epoxyparamethasone was demonstrated. This streamlining allowed for the elimination of isolation and solvent change after each synthetic step. Thus it not only drastically reduced the solvent waste, but also minimized the potential exposure to highly active intermediates thereby increasing the overall yield. The intuitively obvious advantage inherent to lowering the number of solvents was illustrated by applying standard green metrics.