3795-19-5Relevant academic research and scientific papers
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.
Direct Formation of the Steroid Nucleus by a Biomimetic Cyclization
Johnson, William S.,McCarry, Brian E.,Markezich, R. L.,Boots, Sharon G.
, p. 352 - 359 (2007/10/02)
The aim of this study was to synthesize the trienynol 3 and to study its cyclization.The substrate was synthesized by a convergent route, the key step being the stereoselective Wittig-Schlosser condensation of the known aldehyde 19 with the phosphorane 18
Structural requirements for progestational activity. Synthesis and properties of rac-8α,9β,10α,14β-progesterone
Solo,Kumar,Alks,Duax
, p. 129 - 133 (2007/10/18)
rac-8α,9β,10α,14β-progesterone, 1, has been synthesized and subjected to X-ray crystallographic analysis which established that the ring conformations are A, 1β-sofa; B, chair; C, chair; and D, intermediate between an envelope and a half-chair. This compound is 10% as active as progesterone in the Clauberg assay and has an affinity for the uterine cytosol (rabbit) receptor for progesterone 2% as great as that of progesterone.
