86 Prostaglandin及びThromboxane関連化合物の合成

概要

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The prostaglandin endoperoxide (PGG and PGH) and the thromboxane (TX) A_2 are new families of arachidonic acid cascade. The substances were extremely labile and highly biologically active. The chemical synthesis of TX A_2 was not yet achieved. Furthermore, no analogs TX A_2 were not synthesized. In this report we described the synthesis of stable TX A_2 analog and 15-deoxy PG H derivatives. I. Synthesis of PG H analogs PG H analogs were synthesized as follows: a) Treatment of 10, 11 and 12 with hydrogen peroxide and silver trifluoroacetate in ether gave corresponding hydroperoxide; b) resulting substances were cyclized by 3N-NaOH in dichloromethane to give the desired endoperoxide 18, 19 and 20, respectively. II. TX A_2 analog (9,11),(11,12)-dideoxa-(9,11), (11,12)-dimethylene thromboxane A_2 TX A_2 analog was synthesized from bicyclic ketone 23. a) The ketone was converted to the enone 26 in 4 steps. b) Trans fused tricyclic enone 29 was obtained from 26 in 3 steps. c) The compound 29 was oxidized to aldehyde ester 31. d) Introduction of α and β- chain to 31 by the conventional method afforded the desired compound 21. The compound 21 showed the very potent contractile activity on the rat isolated aorta.
天然有機化合物討論会の論文
1979-09-20