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Synfacts 2019; 15(01): 0007
DOI: 10.1055/s-0037-1611377
DOI: 10.1055/s-0037-1611377
Synthesis of Natural Products and Potential Drugs
Synthesis of Prostaglandins F2α and E2
Further Information
Publication History
Publication Date:
14 December 2018 (online)
Key words
prostaglandin F2α - prostaglandin E2 - bicycloheptane - Diels–Alder reaction - Baeyer–Villiger oxidation - iodolactonization
Significance
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.
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Comment
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.
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