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A unified approach to prostanoid and corticosteroid synthons

✍ Scribed by Steven D. Burke; David R. Magnin; Jeffrey A. Oplinger; Julia P. Baker; Ahmed Abdelmagid


Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
321 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis


Synthons for 11-deoxyprostanoids and II-ketosteroids are available via intramolecular Diels-Alder reactions between oxygenated dienes and attached butenolides.

Because of their biological significance, scarcity, and structural diversity, the prostanoid and steroid hormonal agents have held the attention of synthetic chemists for many years.' Reported herein are studies directed at a unified approach to the synthesis of both classes of compounds. The general strategy is based upon the use of the intramolecular Diels-Alder cycloaddition,2 as indicated in eq 1. It was anticipated that the rigid butenolide would effectively transmit dienophile orientation requirements through the tether to the diene, thus favoring the formation of trans-fused hydrindene units as synthons for ll-deoxyprostaglandins and 11-ketosteroids. 3 'H2(1 atm), Lindlar's cat., EtOAc, 25%.


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