A general strategy for the synthesis of taxane diterpenes

Abstract The construction of molecular carbon frameworks stands as the fundamental objective of organic chemistry. The carbon skeleton of each organic molecule serves as the foundation for its three-dimensional structure, playing a pivotal role in determining its physical and biological properties.1 Within the realm of synthesis, the ability to access complex molecules while prioritizing skeletal diversification serves as a crucial factor in advancing the frontiers of efficient synthetic design.2-4 In line with this pursuit, our team has developed a versatile synthetic strategy based on interconversion of complex molecular frameworks which enabled a generalized access to the taxane diterpene family. A wide range of classical and cyclotaxane frameworks was accessed including,among others, the first total syntheses of taxinine K (2), canataxapropellane (5) and dipropellane C from a single advanced intermediate. The synthetic approach deliberately eschews biomimicry, emphasizing instead potency of stereoelectronic control in orchestrating the interconversion of polycyclic frameworks.