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Synthesis of 14-phenylprostaglandins E1, A1 and F2α

✍ Scribed by Robert T. Buckler; David L. Garling


Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
178 KB
Volume
19
Category
Article
ISSN
0040-4039

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✦ Synopsis


In searching for prostaglandins of more specific biological activities, we chose to make analogs having a 14-phenyl substitutent. An examination of space-filling molecular models suggested that such a structural transformation might constrain the lower arm of the PG skeleton in a conformation favoring increased interaction between the two arms. Such interaction would reduce the number of possible conformations and perhaps lead to a sharper profile of pharmacological activities. The synthetic route chosen for the E-type prostaglandins I was based on the conjugate addition of the organ0 cuprate III to the known cyclopentenones II. This reaction is known to


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