抄録
1. The molecular skelton (XIV) of Dendrobine, an alkaloid of Dendrobium nobile Lind1. was synthesized starting from carvotanaceton (I) as shown in Fig 1,3. Carvotanaceton (I) was treated with butadiene to afford the addition product (II), which was converted to unsaturated aldehyde (IV) via diol (III). The compound (XIV) was obtained via (IV)→(VI)→(XIII). Its structure was deduced from the results of n.m.r., mass and infra-red spectra. 2. The potential intermediates for the synthesis of Dendrobine were prepared from the compounds (VI) and (XVIII). (a) The aminoalcohol (XVII) was derived from the above obtained compound (VI) by way of several steps as shown in Fig 4. (b) Isopropyl group was introduced to cis-1-hydroxy-8-methyl-hydrindanone-5 (XVIII) synthesized according the method of C.B.C. Boyce to give the compound (XX) and αβ-unsaturated ketone (XXVII) was obtained by allylic oxidation of the keto olefine (XXV). The intermediate contains carboxyl function (XXXV) was obtained by the hydrocyanation of the αβ-unsaturated ketone and following hydrolysis. Investigations for conversion of the intermediates (XVII) and (XXXVI) to Dendrobine are now in progress.
