Estrogenic and cardiotonic steroidal skeletons were concisely constructed via Mizoroki-Heck and intramolecular Diels-Alder (IMDA) reactions. Simple modification of the dienophile unsaturation of the IMDA precursor enabled representative AB-ring systems of both steroid classes to be accessed from the same intermediate. The diastereoselectivity of the IMDA reaction used to access the cardiotonic steroidal skeleton was found to be significantly enhanced by performing the reaction in water.