Natural and synthetic diastereoisomeric (--)-3',4',7-trihydroxyflavan-3,4-diols.

1. Rhodesian copalwood (Guibourtia coleosperma) contains three diastereo-isomeric leuco-fisetinidins. These consist of the (-)-2,3-cis-3,4-cis (2R,3R,4R) and (-)-2,3-cis-3,4-trans (2R,3R,4S) 3',4',7-trihydroxyflavan-3,4-diols, and the third was shown to be a 2,3-trans-3,4-cis isomer by means of paper ionophoresis. 2. There occurrence in similar proportions as tannin precursors also in the tropical hardwoods G. tessmannii and G. demeusii implies a close taxonomic relationship between these, and with G. coleosperma. 3. Epimerization of the natural (-)-3',4',7- trihydroxy-2,3-trans-flavan-3,4-trans-diol affords a mixture from which the (-)-2,3-cis-3,4-cis isomer was separated readily, but the (-)-2,3-trans-3,4-cis isomer was obtained with difficulty. These were formed by epimerization of the (-)-2,3-trans-3,4-trans isomer at C-2 and C-4, and at C-4, respectively.