Practical F/Δ12,14-D transformation in the prostaglandin series. synthesis of methyl (±)-(5Z,12E,14E)-9α-acetoxy- 16-(3-chlorophenoxy)-15-deoxy-11-oxo-17,18,19,20-tetranorprosta- 5,12,14-trienoate from cloprostenol


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Abstract

Methyl (±)-(5Z,12E,14E)-9α-acetoxy-16-(3-chlorophenoxy)-15-deoxy-11-oxo-17,18,19,20-tetranorprosta- 5,12,14-trienoate was synthesized via selective protection/deprotection of the hydroxy groups in cloprostenol methyl ester, followed by oxidation of the C11–OH group and DBU-promoted elimination of the 9-acetoxy group.

About the authors

N. S. Vostrikov

Ufa Institute of Chemistry

Email: bioreg@anrb.ru
Russian Federation, pr. Oktyabrya 71, Ufa, Bashkortostan, 450054

I. F. Lobko

Ufa Institute of Chemistry

Email: bioreg@anrb.ru
Russian Federation, pr. Oktyabrya 71, Ufa, Bashkortostan, 450054

L. V. Spirikhin

Ufa Institute of Chemistry

Email: bioreg@anrb.ru
Russian Federation, pr. Oktyabrya 71, Ufa, Bashkortostan, 450054

M. S. Miftakhov

Ufa Institute of Chemistry

Author for correspondence.
Email: bioreg@anrb.ru
Russian Federation, pr. Oktyabrya 71, Ufa, Bashkortostan, 450054

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