| Summary: | 碩士 === 臺北市立大學 === 應用物理暨化學系 === 106 === Compound 1 (trans-5-benzoyl-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H- xanthene-6,8-diol) was a new benzophenone component isolated from the leaves of the Tovomita longifolia. Compound 1 showed anticancer activity and antimicrobial activity. Compound 1 has two asymmetric stereocenters in the structure and the absolute stereochemistry has not been determined. Until now, the total synthesis of 1 was not reported yet. The goal of this study is to establish an efficient synthesis method to synthesize compound 1 and its stereoisomers with absolute stereochemistry.
In this study, (R)-citrial and (S)-citrial were prepared from the absolute configuration of (R)-cyclogeranic acid and (S)-cyclogeranic acid in three steps, respectively. Starting from 2-bromo-1,3,5-tris-(methoxymethoxy)benzene and (R)-citrial or (S)-citrial, (4aS,9aR)-23 and (4aR,9aS)-23 with cis configuration were synthesized in four steps. (4aS,9aS)-23 and (4aR,9aR)-23 with trans configuration were further synthesized in four steps from (4aS,9aR)-23 and (4aR,9aS)-23, respectively. The target compound (4aR,9aS)-1 and analogue (4aR,9aS)-13 were successfully synthesized from (4aR,9aS)-23 by benzoylation in presence of ZnBr2. In the same manner, the target compound (4aR,9aR)-1 was successfully synthesized from (4aR,9aR)-23. Other stereoisomers will be synthesized in the due course.
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