45 Quassinoidsの合成研究

概要

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Synthetic studies of quassinoids have been carried out for the purpose of obtaining some informations on the correlation between their structures and antitumor activity. Quassin (4) was transformed in five steps into 5 having the D-ring moiety of bruceantin (2). Inhibitory effect (ID_<50>) against growth of HeLa cells was 150μg/ml for 5, while >200)μg/ml for 4. The Diels-Alder reaction using 6 as a diene and quinone derivatives as dienophiles to form the correponding tricyclic compounds was unsuccessful. The tricyclic compound (12) prepared by Robinson annulation of 10 and 11, which was derived from 7 and 10, was used as starting material. The compound (31) possessing a 14αH-5-picrasene framework has been synthesized in 9 steps from 12 via the ester (28a). This shows a route for available synthesis of quassinoids having a hydroxyl group at C-14 from the ester (28b). The α,β-unsaturated ketone (40) has been synthesized in 5 steps from 12 applying Nakai's carbonyl trans-position method. The syntheses of quassinoids carrying no hydroxyl group at C-14 are under way.
天然有機化合物討論会の論文
1981-09-10