Deuterium-labeled procyanidins have been prepared by hemisynthesis fro
m taxifolin in order to investigate their metabolism in human. The str
uctures of the desired deuterated natural compounds B3 10D (R-1=D, R-2
=H) and B4 13D (R-1=D, R-2=H) were proven by spectroscopic and physica
l properties means, including H-2 NMR spectrum. By-products with unatu
ral absolute configuration at some centers were also formed along the
process and were characterised. (C) 1997 Elsevier Science Ltd.