Synthesis of DL‐Prostaglandin B1 and its reduction product DL‐prostaglandin E1‐237
- 1 January 1968
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 87 (7) , 813-823
- https://doi.org/10.1002/recl.19680870709
Abstract
Coupling of 3‐(2′‐tetrahydropyranyloxy)‐1‐octynylmagnesium bromide with 2‐(6′‐carboxyhexyl)‐2‐cyclopenten‐1‐one followed by Oppenauer oxidation and removal of the protecting group yielded crystalline DL‐2‐(6′‐carboxyhexyl)‐3‐(3′‐hydroxy‐1′‐octynyl)‐2‐cyclopenten‐1‐one. Hydrogenation of the latter substance in the presence of Lindlar's catalyst and subsequent elaidination gave DL‐2‐(6′‐carboxyhexyl)‐3‐(3′‐hydroxy‐1′‐trans‐octenyl)‐2‐cyclopenten‐1‐one ‐ shown to be identical with authentic PGB1 ‐ whereas hydrogenation in the presence of Pd on BaSO4 afforded DL‐2‐(6′‐carboxyhexyl)‐3‐(3′‐hydroxyoctyl)‐2‐cyclopenten‐1‐one known as PGE1‐237.Keywords
This publication has 10 references indexed in Scilit:
- Synthetic studies on prostaglandinsTetrahedron Letters, 1968
- A prostaglandin synthesisTetrahedron Letters, 1967
- Prostaglandins: Members of a New Hormonal SystemScience, 1967
- Prostaglandins II - an improved synthesis and structural proof of (±)-11-deoxyprostaglandin F1βTetrahedron Letters, 1967
- Non‐enzymic conversion of all‐cis 8,11,14‐eicosatrienoic acid into prostaglandin E1Recueil des Travaux Chimiques des Pays-Bas, 1967
- Synthese der Dl‐Form eines natürlichen Prostaglandins. Vorläufige MitteilungHelvetica Chimica Acta, 1967
- Prostaglandins I - total synthesis of 9β,15X-dihydroxyprost-13-enoic acidTetrahedron Letters, 1966
- A Total Synthesis of a Natural ProstaglandinJournal of the American Chemical Society, 1966
- Synthesis of Fatty Acids with Smooth Muscle Stimulant ActivityJournal of Medicinal Chemistry, 1965
- Prostaglandins and Related FactorsJournal of Biological Chemistry, 1963