Wieland–Miescher ketone: a cornerstone in natural product synthesis

Abstract

The Wieland–Miescher ketone (WMK) has cemented its position as a cornerstone in the field of total synthesis, enabling the efficient construction of complex and bioactive natural products. Its characteristic bicyclic enedione framework serves as a versatile chiral pool synthon, facilitating the synthesis of a wide array of terpenoids and alkaloids. While WMK has been a mainstay in total synthesis for decades, this review focuses exclusively on advancements reported since 2014. Highlighting recent methodologies and strategies, we emphasize innovations in enantioselective total synthesis, novel reaction pathways, and applications in the development of pharmaceutically relevant natural products. By examining these modern applications, we aim to underscore the enduring relevance of WMK in addressing challenges in synthesizing intricate natural products.