43119-82-0Relevant articles and documents
Total Synthesis of Limonin
Yamashita, Shuji,Naruko, Akito,Nakazawa, Yuki,Zhao, Le,Hayashi, Yujiro,Hirama, Masahiro
, p. 8538 - 8541 (2015)
Limonoids are highly oxygenated C13α-triterpenes and common secondary metabolites. Several hundred congeners have been isolated to date. The first total synthesis of (±)-limonin, the flagship congener of the limonoids, is now reported and features 1) a tandem radical cyclization generating the BCD ring system with the C13α configuration that is essential to the limonoids and a Robinson annulation to construct the limonoid androstane framework, 2) a singlet-oxygen cycloaddition and a Baeyer-Villiger oxidation to synthesize the highly oxidized D ring, and 3) a Surez reaction to construct the unique AA′ ring system.
Alternative synthetic approaches to rac-progesterone by way of the classic Johnson cationic polycyclization strategy
Slegeris, Rimantas,Dudley, Gregory B.
supporting information, p. 3666 - 3672 (2016/06/06)
Three alternative synthetic entries into Johnson's classic synthesis of rac-progesterone are presented in this manuscript. ent-Progesterone, the non-natural enantiomer of progesterone, has recently been identified as a potential alternative to progesterone for investigations into possible prevention and treatment of traumatic brain injury (TBI). Difficulties in accessing ent-progesterone in large quantities prevent it from being studied more thoroughly. Strategies for producing synthetic rac-progesterone are described and discussed herein.
