A Stereoselective Synthesis of a Stable Prostacyclin Analogue; dl-3-Oxa-9 (Ο)-methano-Δ6 (9α) -prostaglandin I1

KOICHI KOJIMA; KAZUO KOYAMA; SHIGEO AMEMIYA; SHINICHI SAITO

doi:10.1248/cpb.35.948

A Stereoselective Synthesis of a Stable Prostacyclin Analogue; dl-3-Oxa-9 (Ο)-methano-Δ^{6 (9α)}-prostaglandin I₁

KOICHI KOJIMA, KAZUO KOYAMA, SHIGEO AMEMIYA, SHINICHI SAITO

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Keywords: isocarbacyclin, prostacyclin analogue, iodotrimethylsilane, cyclopropane ring, bicyclo [3.3.0] octane

JOURNAL FREE ACCESS

1987 Volume 35 Issue 3 Pages 948-956

DOI https://doi.org/10.1248/cpb.35.948

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Abstract

A prostacyclin analogue, dl-3-oxa-9 (Ο)-methano-Δ^{6 (9α)}-prostaglandin I₁ (1a), has been synthesized. The key step for this synthesis is a new, one-step conversion reaction of the (hydroxymethyl) cyclopropylketone group in 8 and 21 to the γ, δ-unsaturated ketone 9 and 22, respectively, with iodotrimethylsilane.

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