Synthesis of substituted Z-styrenes by Hiyama-type coupling of oxasilacycloalkenes: application to the synthesis of a 1-benzoxocane.

ABSTRACT: Several Hiyama cross-coupling reactions of oxasilacycloalkenes and aryl iodides are described that produce trisubstituted Z-styrenes in moderate to excellent yields. Both electron-rich and electron-poor aryl iodides are tolerated in the cross-coupling reaction. The oxasilacycloalkene coupling partners were prepared by ruthenium-catalyzed intramolecular anti-hydrosilylation of alkynols. One of the cross-coupling products was converted to a 1-benzoxocane, albeit in low yield, using an intramolecular Buchwald-Hartwig etherification. The cyclic ether produced contains the carbon skeleton of heliannuol A.

SUBMITTER: Vyvyan JR 

PROVIDER: S-EPMC5647712 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature