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Paper | Regular issue | Vol 48, No. 12, 1998, pp.2559-2571
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8319
Regioselective Protection of 11-Hydroxy Group and Inversion of Configuration at C-15 in m-Phenylene PGI2 Derivatives

Hisanori Wakita, Yutaka Hosono, and Hiroshi Nagase*

*Basic Research Laboratories, Toray Industries, Inc., 111, Tebiro, Kamakura, Kanagawa, 248, Japan

Abstract

The 15β-hydroxy isomer of a m-phenylene PGl2 derivative was converted to its 15α-hydroxy isomer by regioselective protection of 11-hydroxyl group by acylation using 3,5-dinitrobenzoyl chloride followed by inversion of configuration at C-15. A possibility of the presence of π-π interaction between the benzene ring (electron donor) in m-phenylene PGl2 derivative and that (electron acceptor) in the acid chloride is discussed.