Divergent total syntheses of the hetero-oligomeric iridoid glycosides mainly found in Dipsacus asper were achieved. Thus, loganin (1), which is important as a monomer unit, was efficiently synthesized by stereoselective reductive cyclization using secologanin (2) as a substrate. Sequential condensation reactions of derivatives of 1 and 2 as monomer units led to the first enantioselective total syntheses of the heterooligomers cantleyoside, (E)-aldosecologanin, dipsaperine, (3R, 5S)-5-carboxyvincosidic acid 22-loganin ester, and dipsanoside A.

We have already developed a speech ・ driven embodied entrainment CG character system called " InterActor " which automaticany generates communicative motions and actions such as nods for entrained interaCtion from speech rhythm based on only voice input． Furthermore ， we have developed an advanced system using InterActor which includes the expressed fUnction of motions and emotional expressions from the meaning of utterance by 8peech recognition ， as wen as the entrained fUnction ． In this system ， ta皿【er ' s utterance is converted to text by speech recognition ， and Specfic chara ( ： ter strings are detected from the converted text by adatabase where 105 words 丘〕 r 434 motions and emotional expressions are registered ． Then， the system automaticany generates emotional expressions and motionsthat correspond to the detected character strings ． In this paper， the effectiveness of the system is demonstrated by the sensory evaluation 血 the remote communication experiment for 12 pairs of 24 subjects ， under three conditions ： InterActor ， a CG character with the expressed fUnction ， and InterActor with the expressed 血 nction ( the developed system ) ．

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