Enantioselective total synthesis of(+)-Hydroxyapparicine, potent antimalarial indole alkaloid.

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Hydroxyapparicine was isolated from Tabernaemontana dichotoma in 1984.Then, the relative stereochemistry was proposed that recorded spectral data. However, C15 stereochemistry was not showed. Therefore, absolute stereochemistry of Hydroxyapparicine has never determined. Structure fearture of hydroxyapparicine is 1-azabicyclo[4.2.2] decane and C16 chiral tertiary alchol moiety connected indole 2-position. Moreover, tertiary alchol moiety is unstable under acidic conditions. It was easliy dedydration of similar compound. From synthetic standpiont, synthesis of pseudo-aminal type alkaloids need to novel method under mild conditions. Herein, we repored the stereoselective total synthsis and determination of absolute stereochemistry of 16R-hydroxy-16, 22-dihydroapparicine(Hydroxyapparicine).