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 F and E2

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

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

Publication History

Publication Date:
14 December 2018 (online)



In 1969, Corey and co-workers reported a landmark total synthesis of prostaglandins PGF 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.