Synthesis of Aristotelia-Type Alkaloids. Part XIII. Total syntheses of (+)-makonine, (+)-aristotelinone,and (+)-11,12-didehydroaristoteline |
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Authors: | Reto Stahl Renato Galli Rolf Güller Hans-Jürg Borschberg |
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Abstract: | The oxidative transformation of synthetic (+)-aristoteline ((+)- 6 ) into other metabolites which had been isolated from Aristotelia species was investigated. Thus, treatment of (+)- 6 with I2 as the single oxidant furnished the naturally occurring indole alkaloids (+)-makonine ((+)- 9 ),(+)-aristotelinone ((+)- 11 ), or (+)-11, 12-didehydroaristoteline ((+)- 7 ) in good yields, the selectivity of the oxidation process depending on the chosen reaction conditions. |
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