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Synthesis of highly tritiated 7‐deoxy‐7 dihydroantheridiol and antheriodiol
Author(s) -
Meyer Michael D.,
Carlson Gerald L.,
Toft David O.,
Greaves Austin M.,
Ng KamMui Eva,
McMorris Trevor C.
Publication year - 1987
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.2580240207
Subject(s) - chemistry , chromium trioxide , aldol condensation , butenolide , ketone , chloride , hydrolysis , isopropyl , acetic acid , acetyl chloride , stereochemistry , medicinal chemistry , organic chemistry , chromium , catalysis
Abstract The synthesis of tritiated male‐activating steroids of the aquatic fungus Achlya , 7‐deoxy‐7‐dihydroantheridiol (7‐DA) and antheridiol, has been achieved by aldol condensation of 3β‐acetoxy‐23,24‐dinorchola‐1,5‐dien‐22‐al and the carbanion of 3‐isopropyl‐2‐butenolide. The product with the desired stereochemistry (22S,23R) was isolated and reduced with 3 H 2 in the presence of tris(triphenylphosphine)rhodium chloride. Acid hydrolysis of the acetate gave 1,2[ 3 H ]‐7 DA which had a specific activity of 40 Ci/mmol. 1,2[ 3 H ]‐7 DA was converted to 1,2[ 3 H ]‐antheridiol by protecting the hydroxyl groups as the disilyl ethers, oxidation to the 7‐ketone with chromium trioxide‐dimethylpyrazole and removal of the protecting groups by gentle acid treatment. 1,2[ 3 H ]‐7 DA has been used to detect a protein receptor in the cytosol of Achlya .