Palladium-catalyzed allylation of stable glycal boronates to access multi-substituted C1-glycals: en route to the construction of a spirocyclic core of benthol A

Abstract

C1-Allyl glycal is a type of structural motif prevailing in numerous natural products and bioactive molecules; however, the efficient construction of this scaffold has been less developed. In this study, we have reported a palladium-catalyzed allylation reaction involving stable glycal boronates and allyl bromides under mild conditions, furnishing a variety of structurally diverse C1-allyl glycals in good to excellent yields. By employing this methodology, the total synthesis of pivotal C3–C15 fragments of natural product benthol A was successfully accomplished.