Recent Total Syntheses of Vinigrol

Vinigrol, a natural product first isolated in 1987, has been studied extensively due to its unique structure and biological properties, including antihypertensive and platelet aggregation-inhibiting effects. Vinigrol has a unprecedented 6-6-8 tricyclic ring system with an axial four-carbon bridge, eight contiguous stereocenters, and a strained bicyclo[5.3.1]undecane ring similar to taxol. A combination of the complex structure and impressive pharmacological properties of vinigrol has prompted significant interest from the synthetic community for more than a decade. Early synthetic efforts began in 1993, with numerous failed synthetic approaches by Issam Hanna, Leo A. Paquette and many others. Phil S. Baran and Jon T. Njardarson each completed the total syntheses of vinigrol and a formal total synthesis by Louis Barriault and Krishna P. Kaliappan from 2009 to 2014. In 2019 two successful total syntheses were reported by Chuang-Chuang Li and Tuoping Luo (2^nd generation) followed by a first-generation unsuccessful synthesis by the Luo group in 2024. A complete overview of these syntheses will be provided.