56(PB1-5) D-グリセルアルデヒドアセトニドを用いるアラキドン酸リポキシゲナーゼ代謝産物の合成(ポスター発表の部)

概要

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Optically active aldehydes 1-8 are useful intermediates for synthesis of lipoxin A, lipoxin B, LTA_4, 14,15-LTA_4, LTB_4, 12-epi-LTB_4, and 5-HETE which are lipoxygenase metabolites of arachidonic acid. We synthesized all of these aldehydes 1-8 starting with a readily available single chiral material, D-glyceraldehyde acetonide (10). Our strategy for synthesis of 1-6 is based on the epoxide ring opening reaction of one of the epoxy alcohols 11-14 with an appropriate nucleophile and the transformation of the resulting products into 1-6 via oxidative cleavage of the C(2)-C(3) or C(1)-C(2) carbon bond with IO_4^-. While the aldehydes 7 and 8 were synthesized by diastereoselective epoxidation and subsequent oxidative cleavage (with IO_4^-) of 31 and 35, respectively, which were prepareed by diastereoselective addition reaction of 10 with the corresponding organocopper reagents 15.
天然有機化合物討論会の論文
1987-07-25