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Synthesis of Prostaglandins F2α and E2
Stereo-Controlled Synthesis of Prostaglandins F2α and E2 (dl).
J. Am. Chem. Soc. 1969;
14 December 2018 (online)
Key wordsprostaglandin F2α - prostaglandin E2 - bicycloheptane - Diels–Alder reaction - Baeyer–Villiger oxidation - iodolactonization
In 1969, Corey and co-workers reported a landmark total synthesis of prostaglandins PGF2α and PGE2 which play an important role as hormones in mammalian tissue. Strategic application of a [2.2.1]-bicycloheptane enabled expedient access to the highly substituted cyclopentane core.
Bicycloheptane D was accessed through Diels–Alder reaction between diene B and C. Subsequent Baeyer–Villiger oxidation followed by hydrolysis and iodolactonization furnished lactone G, which was transformed into the natural products by a sequence involving two olefinations.