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Synfacts 2019; 15(01): 0007
DOI: 10.1055/s-0037-1611377
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Prostaglandins F2α and E2

Contributor(s):
Erick M. Carreira
,
Helene Wolleb
Corey EJ. * Weinshenker NM, Schaaf TK, Huber W. Harvard University, Cambridge, USA
Stereo-Controlled Synthesis of Prostaglandins F2α and E2 (dl).

J. Am. Chem. Soc. 1969;
91: 5675-5677
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Further Information

Publication History

Publication Date:
14 December 2018 (online)

 
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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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