Hiyama cross-couplings of oxasilacycloalkenes with aryl iodides provide trisubstituted <i>Z</i>-styrenes in moderate to excellent yield. The oxasilacycloakene coupling partners are prepared by ruthenium-catalyzed intramolecular hydrosilylation of the appropriate alkynols. One of the coupling products was converted to a 1-benzoxocane reminiscent of heliannuol A. Another coupling product was elaborated to the glandulone B skeleton.

Hiyama couplings of oxasilacycloalkenes: Synthesis of trisubstituted Z-styrenes and application to natural product skeletons

253rd National Meeting (2017)

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