75 ロイコトリエンB_4,5(S)-HETE,12(S)-HETEの立体選択的な合成(口頭発表の部)

概要

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Leukotriene B_4 (1) is powerfully chemotactic for macrophages and neutrophiles and therefore relevent to allergic and inflammatory states. Herein we describe a highly stereocontrolled synthesis of 1 in which HPLC separation is not necessary to purify the final product 1 or any intermediates, thus, making it possible to prepare 1 in large quantity. Our synthesis is outlined in Scheme 1. The optically pure key intermediates 6 and 9 are synthesized according to the procedure (eq 1 and 2) in which the kinetic resolution of dl-4 (X = SiMe_3, SnBu_3, I) by the Sharpless asym metric epoxidation plays a central role. The conjugated triene unit of 1 is constructed stereospecifically from the cis enyne 7 (prepareed from 6) and the trans vinyl iodide 9 via vinyl borane 8 according to the procedure reported by Suzuki et al. We also report the synthesis of 5(S)-HETE (2) and 12(S)-HETE (3) as summarized in Scheme 5 and 6. The key intermediates 31 and 38 are prepared in an optically pure form by using eq 1 and 2.
天然有機化合物討論会の論文
1988-09-26