28 Sciadinの立体構造

概要

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The configuration of sciadin, a furanoid diterpene isolated earlier from Sciadopitys verticillata Sieb. et Zucc. has been the subject of the present investigation. N.M.R. spectra of sciadinone(4) and its derivatives clarified the remarkable differences between C-17 H_A and H_B of the series (11). Namely tremendous shifts caused by the different substituents at C-8 were observed only on H_A but not on H_B, and, furthurmore, H_A showed fine splittings (J=1 c.p.s.) due to the coupling with C-1α H whereas H_B did not. (Table 1.). These results were successfully applied to decide to be β-configuration of C-17 H on sciadin.(Table 2). Of the two possible conformations (17 & 18), the latter (=1b) was prefered because of the observation on the large shifts of C-12 H peaks due to C-8-substitution (Table 3.). Configurations of several other sciadin derivatives have also been discussed.
天然有機化合物討論会の論文
1966-09-15