A unified approach to prostanoid and corticosteroid synthons
β 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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β¦ 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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