Owing to their interesting biological activity and architectural complexity, Daphniphyllum alkaloids have triggered intensive research activities from the synthetic community. Nine types of Daphniphyllum alkaloids, such as daphniphylline-type, daphmanidin A-type, calyciphylline A-type, and yuzurimine-type alkaloids, have been accessed by total synthesis over past decades. However, more than twenty types of Daphniphyllum alkaloids remain inaccessible by chemical synthesis. Here, we wish to describe our recent efforts toward the total synthesis of daphniglaucin-C type alkaloids, namely, daphnimacropodines. Key features of our synthesis include a Robinson annulation and a Simmons-Smith cyclopropanation that constructed the pivotal vicinal quaternary centers, and a Horner-Wadsworth-Emmons reaction that forms the critical cyclopentene motif. (C) 2021 Elsevier Ltd. All rights reserved.