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Paper | Special issue | Vol 30, No. 1, 1990, pp.617-626
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S74
A Highly Stereoselective Synthesis of Methoxycarbonyl-Substituted Exocyclic Enol Ethers: A Synthesis of 5-Methoxycarbonylprostacyclin

Atsuo Takahashi, Chika Yamamoto, and Masakatsu Shibasaki*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan

Abstract

Treatment of the diene 9 with a catalytic amount of 10% Pd-C in toluene at -50°C under H2 (1 atm) afforded the E-methoxycarbonylsubstituted exocyclic enol ether 10E in a highly stereoselective manner (E:Z=41:1, 98%). 10E was successfully transformed into 5-methoxycarbonylprostacyclin (5).