Alternative synthetic approaches to rac-progesterone by way of the classic Johnson cationic polycyclization strategy

• Published in: Tetrahedron Vol. 72; no. 26; pp. 3666 - 3672
• Main Authors: Slegeris, Rimantas, Dudley, Gregory B.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 30-06-2016
• Subjects: Alkene synthesis; Brain; Cationic; Enantiomers; Injury prevention; Process improvement; Progesterone; Strategy; Synthesis; Tetrahedrons; Total synthesis; Traumatic brain injury (TBI); Alkene synthesis; Traumatic brain injury (TBI); Progesterone; Process improvement; Total synthesis
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2016.03.041

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.
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