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Communication | Special issue | Vol 13, No. 1, 1979, pp.163-167
Published online, 1st January, 1970
DOI: 10.3987/S-1979-01-0163
Terrein, an Optically Active Prostaglandin Synthon of Fungal Origin. III. Chemical Conversion to 1(S), 4(R), 7(R)-Acetoxy-5(S)-hydroxy-2-oxabicyclo [2.2.1]heptan-3-one, a Flexible Intermediate for Prostaglandin Synthesis

George W. Clark, III, Paul D. Hammesfahr, P. Bryan Hudson, Lester A. Mitscher,* Kunikatsu Shirahata, Jerzy Sulko, and Tarik Veysoglu

*Department of Medicinal Chemistry, The University of Kansas, Lawrence, Kansas 66045, U.S.A.


1(S),4(R),7(R)-Acetoxy-5(S)-hydroxy-2-oxabicyclo[2.2.1]heptane-3-one (2), a flexible intermediate for the synthesis of novel optically active prostaglandins, has been synthesized from the optically active and readily available mold metabolite, terrein (1). Some reactions of 2 are described.