53 生合成類似経路によるプロスタグランジンの合成

概要

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Prostaglandin E_1 has been synthesized from an eicosatrienoic acid deravative via a biomimetic pathway. Treatment of a model compound 3 with Hg(OCOCF_3)_2 in CH_3NO_2 followed by addition of KBr gave a cyclopentane derivative 12 stereoselectively, except for stereochemistry at C-15(PG-numbering). Similarly compound 23 which was prepared through a route shown in Fig. 3 was converted to a prostene derivative 24 in good yield. The epimers at C-15 of 24 were separated by column chromatography and inversion of configuration of the hydroxyl groups at C-11 of both epimers and at C-15 of the 15β, epimer was effected by treatment with diethyl azodicarboxylate, triphenylphosphine and acetic acid to give 25, as shown in Fig. 4. The acetyl groups of 25 was then replaced by tert-butyldimethylsilyl groups and the mercuric function of the product was substituted by a hydroxy group (NaBH_4,O_2, DMF). The resulting masked prostanoid 27 was converted to dl-PGE_1 via three steps (Fig. 4) in good overall yield.
天然有機化合物討論会の論文
1981-09-10