Prostaglandin F2 alpha

Emphasis on E.J. Corey strategy. Includes History, Retro.

1. SEMINAR PRESENTATION 1 PROSTAGLANDIN F2 α By E.J. COREY Presentation By: Soham Thakur Integrated M.Sc. Chemistry B.Ed. 2018IMSBCH014 1

2. INTRODUCTION Isolation from human semen by Von Euler Ulf von Euler Source: Wikipedia Euler discovered Prostaglandin in 1930s. Isolation and structure determination by Sune K. Bergstr ö m in 1950s. Synthesized in cell from Arachadonic acid Sune K. Bergstr ö m Source: nobelprize.org Euler U.S., J. Physiol., 1936, 213-234 Bergstr ö m et al., Acta Chem. Scand., 14 , 1960, 1693-1700 Source: https://pubchem.ncbi.nlm.nih.gov/compound/Arachidonic-acid 2

3. Name Prostaglandin F2 α “Prostaglandin” = Prosta + Glandin :: Derived from Prostate Gland ? ? 3

4. BIOLOGICAL APPLICATIONS Organs PGF2 α Blood Vessels Large Vessels Contract Uterus In Vivo & In Vitro contraction and softening of Cervix Bronchi Constriction Intestine Spasmogenic https://www.medicinenet.com/script/main/art.asp?articlekey=39804 4

5. Total Synthesis By E. J. Corey Retrosynthetic Analysis: PGF2 α 5 Classics in Total Synthesis , Nicolau K. C. , Sorenson E. J. , Wiley , 65-82

6. 6 Classics in Total Synthesis , Nicolau K. C. , Sorenson E. J. , Wiley , 65-82

7. Total Synthesis: 7 Classics in Total Synthesis , Nicolau K. C. , Sorenson E. J. , Wiley , 65-82

8. 8 Classics in Total Synthesis , Nicolau K. C. , Sorenson E. J. , Wiley , 65-82

9. 9 Classics in Total Synthesis , Nicolau K. C. , Sorenson E. J. , Wiley , 65-82

10. 10 Classics in Total Synthesis , Nicolau K. C. , Sorenson E. J. , Wiley , 65-82

11. INDUSTRIAL SYNTHESIS Starting Material: Key Step: Aldol Cascade Reaction Advantages: High control of relative and absolute stereochemistry Involves only SEVEN steps Reduces wastes, time, cost Coulthard et al, Nature, 489,  2012, 278–281 11

12. APPLICATIONS Medication: Treatment of atrophic cutaneous scarring Healing of corneal and conjunctival lesions Stimulates the muscle growth Forensic Science: Menstructural blood marker Warren J. Schrer , US10039770B2 , US Patent Jean Sebastien Garrigue , US9555045B2 , US Patent Horsley V, Pavlath G.K., J. Cell Biol., 2003, 161(1): 111–118 Varukha K.V., Med. Sc. Ukraine, 2019 , Vol 15 No 1-2 12

13. 13 THANK YOU