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17,18‐tritium labeled prostaglandins
Author(s) -
Hsi Richard S. P.
Publication year - 1978
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580140406
Subject(s) - chemistry , tritium , lactone , triphenylphosphine , prostaglandin , diol , tritium illumination , chloride , ether , tris , medicinal chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , physics , nuclear physics
The triple bond in 3α,5α‐dihydroxy‐2β‐(3α‐hydroxy‐ trans ‐1‐octen‐5‐ynyl)‐lα‐cyclopentylacetic acid γ‐lactone bis ‐2‐tetrahydropyranyl ether (I) was reduced with tritium gas in the presence of tris ‐(triphenylphosphine) ‐rhodium chloride to give 3α,5α‐dihydroxy‐2β‐(3α‐hydroxy‐5,5,6,6‐tetratritio‐ trans ‐l‐octenyl)‐lα‐cyclopentylacetic acid γ‐lactone (II). The diol‐lactone II was converted in five steps via modified Corey synthesis to prostaglandin E 2 ‐17,18‐ 3 H 4 (VI). Reduction of VI gave prostaglandin E 1 ‐17,18‐ 3 H 4 (VII) and its 13,14‐dihydro (VIII) and 13,14‐dihydro‐15‐dehydro (IX) derivatives. The prostaglandin E's were dehydrated to afford the corresponding tritium labeled prostaglandins A 2 (X) and A 1 (XI).